Compounds for inhibiting EGFR and synthesis method of the compounds

Specific 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one compounds address the limitations of existing EGFR inhibitors by providing selective and effective cancer treatment with reduced side effects through targeted synthesis.

WO2025144340A1PCT designated stage Publication Date: 2025-07-03HACETTEPE UNIVERSITESI REKTORLUK +1
View PDF 1 Cites 0 Cited by

Patent Information

Application Number
PCT/TR2024/051756
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Filing Date
2024-12-25
Publication Date
2025-07-03

AI Technical Summary

Technical Problem

Current cancer treatments using EGFR inhibitors face challenges such as severe side effects and resistance development, necessitating the need for new compounds with reduced side effects and improved selectivity for cancer cells.

Method used

Development of specific 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one compounds that inhibit EGFR, designed to target cancer cells more selectively and synthesized using a method compatible with green chemistry principles.

Benefits of technology

The compounds demonstrate effective EGFR inhibition with reduced side effects and improved selectivity for cancer cells, enhancing treatment efficacy while minimizing harm to normal cells.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure TR2024051756_03072025_PF_FP_ABST
    Figure TR2024051756_03072025_PF_FP_ABST
Patent Text Reader

Abstract

The present invention relates to specific 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one compounds (4a-17z) which enable EGFR (Epidermal Growth Factor Receptor) inhibition, which is known to be involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition, and to a synthesis method (100) of the compounds (4a-17z).
Need to check novelty before this filing date? Find Prior Art

Description

[0001]DESCRIPTION COMPOUNDS FOR INHIBITING EGFR AND SYNTHESIS METHOD OF THE COMPOUNDS Technical Field The present invention relates to specific 2-substituted-5-arylidenethiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one compounds which enable EGFR (Epidermal Growth Factor Receptor) inhibition, which is known to be involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition, and to a synthesis method of the compounds. Background of the Invention Cancer is a fatal disease group that starts with the uncontrolled division of cells as a result of DNA damage, may occur in almost any tissue or organ, and may spread to other tissues and organs through metastasis. According to World Health Organization (WHO) reports, 9.6 million people lost their lives in 2018 due to cancer, which is quite old and deadly for humanity, and it is predicted that 13 million people will lose their lives due to this disease in 2030. With these data from WHO, cancer has taken the second place in the list of the most common causes of death in the world. Although there are different treatment options depending on the stage of the disease and the condition of the patient, chemotherapy still remains the first choice in the treatment of many types of cancer. Although various drugs with different chemical structures are effectively used in cancer treatment, the discovery of new drugs in this field remains important due to the serious side effects, selective effect problems and resistance development potential of existing drugs. The European patent document no. EP3205650, an application included in the state of the art, discloses a series of EGFR inhibitors represented by formula (I) and a preparation and application thereof. Within the scope of the said invention, 4- substituted-2-(N-(5-allylamido)phenyl)amino)pyrimidine derivatives which have activity of inhibiting EGFR were found. The said compounds can be used alone or in part to treat diseases mediated by the activity of the EGFR mutant, the EGFR- L858R mutant, the EGFR-T790M mutant and the mutant activated by exon 19 deletion. For example, these derivatives are intended to have a wide use in preventing and treating cancer, particularly non-small cell lung cancer. An object of the present invention is to realize derivatives and synthesis of specific 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one which enables EGFR (Epidermal Growth Factor Receptor) inhibition, which is known to be involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition. Another object of the present invention is to achieve new compounds with reduced side effects by design and synthesis of new drug candidate compounds that aim to affect cancer cells relatively more selectively compared to normal cells with targeted drug design in cancer treatment. A further object of the present invention is to design and synthesize EGFR inhibitor effective compounds, which are involved in the pathophysiology of cancer disease that has been studied extensively and for which rational treatment is not certain. A further object of the present invention is to realize the synthesis of specific 2- substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one derivatives successfully and with high efficiency. A further object of the present invention is to ensure that the synthesis of molecules is easy to carry out. A further object of the present invention is to ensure that the synthesis and purification protocols of the compounds are compatible with green chemistry applications. Detailed Description of the Invention “Compounds For Inhibiting EGFR and Synthesis Method of The Compounds” realized to fulfil the objectives of the present invention is shown in the figures attached, in which: Figure 1 is a flowchart of the inventive method. Figure 2 shows the reactions occurring during the synthesis of specific 2- substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one derivatives. Figure 3 shows the 2-substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one compounds (4a-17z) obtained by the inventive method. Figure 4 shows the result of the Western Blot test of compound 6z. Figure 5 shows the result of the Western Blot test of compound 6t. Figure 6 shows the inhibitory effects (IC50 values) of some compounds on EGFR of which activity studies were carried out. The present invention relates to 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4- triazole-6(5H)-one derivative compounds (4a-17z) which have the formula (I) that enables EGFR inhibition, which is involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition. The compounds of the inventive formula (I) are (Z)-5-Benzylidene-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4a), (Z)-5-(4- FloroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (4b), (Z)-5-(2-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (4c), (Z)-5-(4-Chlorobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (4d), (Z)-5-(2,4- Dichlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (4e), (Z)-5-(4-Bromobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4f), (Z)-5-(3- NitroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (4g), (Z)-5-(4-NitroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (4h), (Z)-5-(4-MethylBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4i), (Z)-5-(4- Trifluoromethylbenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (4j), (Z)-5-(2-Methoxybenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4k), (Z)-5-(4- MethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (4l), (Z)-5-(2,3-DimethoxyBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol- 6(5H)-one (4n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (4o), (Z)-5-(3,4,5- Trimethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (4p), (Z)-5-(2-Bromo-5-methoxybenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (4r), (Z)-5-(4- Trifluoromethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4t), (Z)-5-(2-Chloro-5- nitrobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (4u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4v), (Z)-5-(4- DimethylamineBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4y), (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]- 2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x2), (Z)-5- [5-(2,5-(5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (4x3), (Z)-5-[5-(3,4- Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x4), (Z)-5-[5-(2-Nitrophenyl)furan-2-il-Methylen]-2- (3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x6), (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2- (3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x7), (Z)-5-[(1- Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2- (3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4x10), (Z)-5-Benzylidene-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5a), (Z)-5-(4- Fluorobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (5b), (Z)-5-(2-ChloroBenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5c), (Z)-5-(4- ChloroBenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (5d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5e), (Z)-5-(4- Bromobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (5f), (Z)-5-(3-Nitrobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (5g), (Z)-5-(4- Nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)- one (5h), (Z)-5-(4-Methylbenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5i), (Z)-5-(4-TrifloroMethylBenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5j), (Z)-5-(2- MethoxyBenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (5k), (Z)-5-(4-Methoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5l), (Z)-5-(2,3- Dimethoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (5m), (Z)-5-(2,5-Dimethoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5n), (Z)-5-(3,4- DimethoxyBenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol- 6(5H)-one (5o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (5p), (Z)-5-(2-Bromo- 5-methoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (5r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (5s), (Z)-5-(4-Chloro- 3-trifluoromethylbenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5t), (Z)-5-(2-Chloro-5-nitroBenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5u), (Z)-5-(4-Chloro-3- nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (5v), (Z)-5-(4-Dimethylaminebenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5y), (Z)-5-(4- Dimethylamine-2-nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2-il- Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x3), (Z)-5-[5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]-2- (3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x6), 5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2- (3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x9), (Z)-5-(2,3-MethylendioxyBenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5x10), (Z)-5- Benzylidene-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6a), (Z)-5-(4-Fluorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (6b), (Z)-5-(2-Chlorobenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6c), (Z)-5-(4- Chlorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (6d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6e), (Z)-5-(4- BromoBenzylidene)-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (6f), (Z)-5-(3-NitroBenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6g), (Z)-5-(4- Nitrobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (6h), (Z)-5-(4-Methylbenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6i), (Z)-5-(4- Trifluoromethylbenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6j), (Z)-5-(2-Methoxybenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6k), (Z)-5-(4- Methoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (6l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (6m), (Z)-5-(2,5- Dimethoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (6n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (6p), (Z)-5-(2-Bromo-5-MethoxyBenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6r), (Z)-5-(4- Trifluoromethoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (6s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2- (3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6t), (Z)-5- (2-Chloro-5-nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (6u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6v), (Z)-5-(4- Dimethylaminebenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (6y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (6x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]- 2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (6x2), (Z)- 5-[5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (6x4), (Z)-5-[5-(2-Nitrophenyl)furan-2-il-Methylen]-2- (3,4,5-triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (6x6), (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2- (3,4,5-triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (6x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2- (3,4,5-triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (6x10), (Z)-5-Benzylidene-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7a), (Z)-5-(4- Fluorobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (7b), (Z)-5-(2-Chlorobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7c), (Z)-5-(4- Chlorobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (7d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7e), (Z)-5-(4- Bromobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (7f), (Z)-5-(3-Nitrobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7g), (Z)-5-(4- Nitrobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (7h), (Z)-5-(4-MethylBenzylidene)-2-(2,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (7i), (Z)-5-(4-TrifloroMethylBenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7j), (Z)-5-(2- Methoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (7k), (Z)-5-(4-Methoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7l), (Z)-5-(2,3- Dimethoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (7m), (Z)-5-(2,5-Dimethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (7n), Z)-5-(3,4- Dimethoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (7o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (7p), (Z)-5-(2- Bromo-5-methoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (7r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (7t), (Z)-5-(2-Chloro-5-nitrobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7u), (Z)-5-(4- Chloro-3-nitrobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (7v), (Z)-5-(4-Dimethylaminebenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7y), (Z)-5-(4- Dimethylamine-2-nitrobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (7z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-(2,5-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (7x2), (Z)-5-[5-(2,5-Dichlorophenyl)furan-2-yl- methylene]-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x3), (Z)-5-[5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-(2,5-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (7x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]-2- (2,5-Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(2,5-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (7x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2- (2,5-Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-(2,5-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (7x9), (Z)-5-(2,3-MethylendioxyBenzylidene)-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7x10), (Z)-5- Benzylidene-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8a), (Z)-5-(4-Fluorobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (8b), (Z)-5-(2-Chlorobenzylidene)-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8c), (Z)-5-(4- ChloroBenzylidene)-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (8d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8e), (Z)-5-(4- Bromobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (8f), (Z)-5-(3-Nitrobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8g), (Z)-5-(4- Nitrobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (8h), (Z)-5-(4-MethylBenzylidene)-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (8i), (Z)-5-(4-TrifloroMethylBenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8j), (Z)-5-(2- Methoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (8k), (Z)-5-(4-Methoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8l), (Z)-5-(2,3- Dimethoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (8m), (Z)-5-(2,5-Dimethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (8n), (Z)-5-(3,4- Dimethoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (8o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (8p), (Z)-5-(2- Bromo-5-methoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (8r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (8t), (Z)-5-(2-Chloro-5-nitrobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8u), (Z)-5-(4- Chloro-3-nitrobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (8v), (Z)-5-(4-Dimethylaminebenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8y), (Z)-5-(4- Dimethylamine-2-nitrobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (8z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-(3,4-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (8x2), (Z)-5-[5-(2,5-Dichlorophenyl)furan-2-yl- methylene]-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x3), (Z)-5-[5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (8x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]-2- (3,4-Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (8x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2- (3,4-Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (8x9), (Z)-5-(2,3-MethylendioxyBenzylidene)-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8x10), 5-Benzylidene- 2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9a), (Z)-5- (4-Fluorobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (9b), (Z)-5-(2-Chlorobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9c), (Z)-5-(4- Chlorobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (9d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9e), (Z)-5-(4- Bromobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (9f), (Z)-5-(3-Nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9g), (Z)-5-(4- Nitrobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (9h), (Z)-5-(4-MethylBenzylidene)-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9i), (Z)-5-(4- Trifluoromethylbenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (9j), (Z)-5-(2-Methoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9k), (Z)-5-(4- Methoxybenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (9l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-(2-trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol- 6(5H)-one (9n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9o), (Z)-5- (3,4,5-Trimethoxybenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (9p), (Z)-5-(2-Bromo-5-methoxybenzyl- den)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9r), (Z)-5-(4- Trifluoromethoxybenzyl- den)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (9s), (Z)-5-(4-Chloro-3-trifloroMethylBenzylidene)-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9t), (Z)-5-(2- Chloro-5-nitrobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (9u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9v), (Z)-5-(4- Dimethylaminebenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (9y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9z), (Z)-5-[5- Phenylfuran-2-yl-methylene]-2-(2-trifluoromethylphenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (9x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]- 2-(2-trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x2), (Z)-5- [5-(2,5-(5-Dichlorophenyl)furan-2-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9x3), (Z)-5-[5- (3,4-Dichlorophenyl)furan-2-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(2-trifloroMethylfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (9x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]-2- (2-trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(2-trifloroMethylfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (9x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x8), (Z)-5-[(2- Methyl)-1H-indol-3-yl-methylene]-2-(2-trifluoromethylphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (9x9), (Z)-5-(2,3-Methylenedioxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9x10), (Z)-5- Benzylidene-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10a), (Z)-5-(4-FloroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (10b), (Z)-5-(2-ChloroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (10c), (Z)-5-(4-ChloroBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10d), (Z)-5-(2,4- DiChloroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (10e), (Z)-5-(4-BromoBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (10f), (Z)-5-(3-NitroBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10g), (Z)-5-(4- NitroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10h), (Z)-5-(4-MethylBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (10i), (Z)-5-(4-Trifluoromethylbenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10j), (Z)-5-(2- Methoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)- one (10k), (Z)-5-(4-Methoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (10l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (10m), (Z)-5-(2,5- Dimethoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b][1,2,4]triazole- 6(5H)-one (10n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)- one (10p), (Z)-5-(2-Bromo-5-methoxybenzyl- den)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10r), (Z)-5-(4- Trifluoromethoxybenzyl- den)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (10s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10t), (Z)-5-(2-Chloro-5- nitrobenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (10v), (Z)-5-(4-Dimethylaminebenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10y), (Z)-5-(4- Dimethylamine-2-nitroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (10z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(4- siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2-il- Methylen]-2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x3), (Z)-5-[5-(3,4-Dichlorophenyl)furan-2-yl-methylene]-2-(4- cyanophenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (10x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-yl-methylene]-2-(4-cyanophenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]- 2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2- (4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x9), (Z)-5-(2,3-MethylendioxyBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10x10), (Z)-S-(5- Benzylidenethiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il)Methyl ethanoate (11a), (Z)-S-[5-(4-FloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11b), (Z)-S-[5-(2-ChloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-on-2-il]Methyl ethanoate (11c), (Z)-S-[5-(4- ChloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11d), (Z)-S-[5-(2,4-DiChloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on- 2-il]Methyl ethanoate (11e), (Z)-S-[5-(4-BromoBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11f), (Z)-S-[5-(3- NitroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11g), (Z)-S-[5-(4-Nitrobenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2- yl]methyl ethanoate (11h), (Z)-S-[5-(4-Methylbenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11i), (Z)-S-[5-(4- TrifloroMethylBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11j), (Z)-S-[5-(2-MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-on-2-il]Methyl ethanoate (11k), (Z)-S-[5-(4- MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11l), (Z)-S-[5-(2,3-Dimethoxybenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-yl]methyl ethanoate (11m), (Z)-S-[5-(2,5- Dimethoxybenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11n), (Z)-S-[5-(3,4-DimethoxyBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11o), (Z)-S-[5-(3,4,5- TriMethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11p), (Z)-S-[5-(2-Bromo-5-MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-yl]methyl ethanoate (11r), (Z)-S-[5-(4- Trifluoromethoxybenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11s), (Z)-S-[5-(4-Chloro-3-Trifluoromethylbenzylidene)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11t), (Z)-S-[5-(2-Chloro- 5nitroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11u), (Z)-S-[5-(4-Chloro-3-nitrobenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- on-2-yl]methyl ethanoate (11v), (Z)-S-[5-(4- Dimethylaminebenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11y), (Z)-S-[5-(2-Nitro-4-Dimethylaminebenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11z), (Z)-S-[5-(5-Phenylfuran-2-il- Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x1), (Z)-S-[5-(5-(4-Chlorophenyl)furan-2-il-Methylen)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-on-2-il]Methyl ethanoate (11x2), (Z)-S-[5-(5-(2,5-DiChlorophenyl)furan-2- il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x3), (Z)-S-[5-(5-(3,4-DiChlorophenyl)furan-2-il-Methylen)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11x4), (Z)-S-[5-(5-(3-Nitrophenyl)furan- 2-il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x5), (Z)-S-[5-(5-(4-Nitrophenyl)furan-2-il-Methylen)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11x6), (Z)-S-[5-((1-Acetyl)-1H-indol-3-il- Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x7), (Z)-S-[5-((1-Methyl)-1H-indol-3-il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- on-2-yl]methyl ethanoate (11x8), (Z)-S-[5-((2-Methyl)-1H-indol-3-yl- methylene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11x9), (Z)-S-[5-(2,3-Methylenedioxybenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on- 2-yl]methyl ethanoate (11x10), (Z)-5-Benzylidene-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12a), (Z)-5-(4- FloroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12b), (Z)-5-(2-ChloroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12c), (Z)- 5-(4-ChloroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (12d), (Z)-5-(2,4-DiChloroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12e), (Z)- 5-(4-BromoBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (12f), (Z)-5-(3-NitroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12g), (Z)- 5-(4-NitroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12h), (Z)-5-(4-MethylBenzylidene)-2-[3-(2,5- dimethoxyphenyl)-3-oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12i), (Z)-5-(4-Trifluoromethylbenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12j), (Z)-5-(2- MethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12k), (Z)-5-(4-MethoxyBenzylidene)-2-[3-(2,5- dimethoxyphenyl)-3-oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-[3-[3-(2,5- dimethoxyphenyl)-3-oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12r), (Z)-5-(4-TrifloroMethoxyBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12s), (Z)- 5-(4-Chloro-3-trifloroMethylBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (12u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12v), (Z)- 5-(4-DimethylamineBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12y), (Z)-5-(4-Dimethylamine- 2-nitroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x6), (Z)-5-[(1-Acetyl)-1H- indol-3-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2-[3- (2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x10), (Z)-5-Benzylidene-2- (2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13a), (Z)- 5-(4-FloroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13b), (Z)-5-(2-ChloroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13c), (Z)-5-(4- ChloroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13e), (Z)-5-(4- Bromobenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13f), (Z)-5-(3-NitroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13g), (Z)-5-(4- NitroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (13h), (Z)-5-(4-MethylBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13i), (Z)-5-(4- Trifluoromethylbenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (13j), (Z)-5-(2-Methoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13k), (Z)-5-(4- MethoxyBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13m), (Z)-5-(2,5- Dimethoxybenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13n), (Z)-5-(3,4-DimethoxyBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (13p), (Z)-5-(2-Bromo-5-methoxybenzylidene)-2-(2- nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13r), (Z)- 5-(4-Trifluoromethoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13t), (Z)-5-(2-Chloro- 5-nitroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13v), (Z)-5-(4- DimethylamineBenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (13y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)-2-(2- nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13z), (Z)- 5-[5-Phenylfuran-2-il-Methylen]-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (13x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il- Methylen]-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (13x2), (Z)-5-[5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(2-nitro- 4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x3), (Z)-5-[5- (3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (13x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]- 2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x6), (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x7), (Z)-5-[(1- Methyl)-1H-indol-3-il-Methylen]-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (13x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2- (2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13x9), (Z)-5-(2,3-Methylenedioxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x10), (Z)-5- Benzylidene-2-[2-(2-butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (14a), (Z)-5-(4-FloroBenzylidene)-2-[2-(2-butyl-amino)- 2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14b), (Z)-5-(2- ChloroBenzylidene)-2-[2-(2-butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (14c), (Z)-5-(4-ChloroBenzylidene)-2-[2-(2-butyl- amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14d), (Z)-5-(2,4-DiChloroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14e), (Z)-5-(4- BromoBenzylidene)-2-[2-(2-butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (14f), (Z)-5-(3-NitroBenzylidene)-2-[2-(2-butyl- amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14g), (Z)-5-(4-NitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14h), (Z)-5-(4- MethylBenzylidene)-2-[2-(2-butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (14i), (Z)-5-(4-TrifloroMethylBenzylidene)-2-[2-(2- butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14j), (Z)-5-(2-MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14k), (Z)-5-(4- MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14l), (Z)-5-(2,3- DimethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14n), (Z)-5-(3,4- Dimethoxybenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14o), (Z)-5-(3,4,5- Trimethoxybenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14p), (Z)-5-(2- Bromo-5-MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14r), (Z)-5-(4- TrifloroMethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14s), (Z)-5-(4- Chloro-3-trifloroMethylBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14t), (Z)-5-(2- Chloro-5-nitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14u), (Z)-5-(4- Chloro-3-nitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14v), (Z)-5-(4- Dimethylaminebenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14y), (Z)-5-(4- Dimethylamine-2-nitrobenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x2), (Z)-5-[5- (2,5-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x3), (Z)-5-[5- (3,4-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x7), (Z)-5-[(1- Methyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x10), (Z)-5- Benzylidene-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (15a), (Z)-5-(4-FloroBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15b), (Z)-5-(2- ChloroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15c), (Z)-5-(4-ChloroBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15d), (Z)-5-(2,4- DiChloroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15e), (Z)-5-(4-BromoBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15f), (Z)-5-(3-NitroBenzylidene)- 2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15g), (Z)-5-(4-NitroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15h), (Z)-5-(4-MethylBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15j), (Z)-5-(2-MethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15k), (Z)-5-(4- MethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15l), (Z)-5-(2,3-DimethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15m), (Z)-5- (2,5-DimethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15n), (Z)-5-(3,4-DimethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15o), (Z)-5- (3,4,5-TriMethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15p), (Z)-5-(2-Bromo-5-MethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15r), (Z)-5-(4- Trifluoromethoxybenzylidene)-2-[2-(5-phenyloxazol-2-yl)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2- [2-(5-phenyloxazol-2-yl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15t), (Z)-5- (2-Chloro-5-nitroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15v), (Z)-5-(4- DimethylamineBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15y), (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-[2- (5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15z), (Z)-5- [5-Phenylfuran-2-il-Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]-2- [2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (15x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il-Methylen]- 2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x6), (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x7), (Z)-5-[(1-Methyl)-1H- indol-3-il-Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15x10), (Z)-5-Benzylidene-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16a), (Z)-5-(4- FloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16b), (Z)-5-(2-ChloroBenzylidene)-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16c), (Z)-5-(4- ChloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16d), (Z)-5-(2,4-DiChloroBenzylidene)-2-[2-(5-phenyl- 1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16e), (Z)-5- (4-BromoBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (16f), (Z)-5-(3-NitroBenzylidene)-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16g), (Z)-5-(4- NitroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16h), (Z)-5-(4-MethylBenzylidene)-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16j), (Z)-5-(2- MethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16k), (Z)-5-(4-MethoxyBenzylidene)-2-[2-(5-phenyl- 1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16l), (Z)-5- (2,3-DimethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (16n), (Z)-5-(3,4-DimethoxyBenzylidene)-2-[2-(5- phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16o), (Z)-5-(3,4,5-TriMethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16r), (Z)-5-(4-TrifloroMethoxyBenzylidene)-2-[2-(5- phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16s), (Z)-5-(4-Chloro-3-trifloroMethylBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2-[2-(5- phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16v), (Z)-5-(4-DimethylamineBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16y), (Z)-5-(4-Dimethylamine-2- nitroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-[2-(5- phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole- 2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x6), (Z)-5-[(1-Acetyl)-1H- indol-3-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (16x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2-[2- (5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x10), (Z)-5-Benzylidene-2-[2- (6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17a), (Z)-5-(4-FloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17b), (Z)-5-(2- ChloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17c), (Z)-5-(4-ChloroBenzylidene)-2-[2-(6-bromo-4- oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17d), (Z)-5- (2,4-DiChloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17e), (Z)-5-(4- BromoBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17f), (Z)-5-(3-NitroBenzylidene)-2-[2-(6-bromo-4- oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17g), (Z)-5- (4-NitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17h), (Z)-5-(4-MethylBenzylidene)-2-[2-(6-bromo-4- oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17i), (Z)-5- (4-TrifloroMethylBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17j), (Z)-5-(2- MethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17k), (Z)-5-(4-MethoxyBenzylidene)-2-[2-(6-bromo-4- oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17l), (Z)-5- (2,3-DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17n), (Z)-5-(3,4- DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17r), (Z)-5-(4-TrifloroMethoxyBenzylidene)-2-[2-(6- bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17s), (Z)-5-(4-Chloro-3-trifloroMethylBenzylidene)-2-[2-(6-bromo-4-oxo-4H- chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17t), (Z)-5-(2- Chloro-5-nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17u), (Z)-5-(4-Chloro-3- nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (17v), (Z)-5-(4-DimethylamineBenzylidene)-2-[2-(6- bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17y), (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H- chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x6), (Z)-5-[(1-Acetyl)-1H- indol-3-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (17x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2- [2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (17x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-[2-(6-bromo-4-oxo-4H- chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x10). The inventive compounds are pharmaceutical formulation / composition containing any compound of Formula (I). The inventive compounds are drugs containing any compound of Formula (I). 100. Method Synthesis method (100) of the inventive specific 2-substituted-5- arylidenethiazolo[3,2-b]-1,2,4-triazole-6(5H)-one derivatives, which enable EGFR inhibition, which is involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition comprises the steps of - synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); - synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); - synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); and - synthesizing 2-substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one compounds (4a-17z) from suitable triazole compounds (4-17) (104). In the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101) of the inventive method (100), a 30 mmol of carboxylic acid compound (1 (R1-COOH)) is dissolved with a 30-40 mL of tetrahydrofuran and the mixture is prepared by adding N-hydroxysuccinimide dissolved in tetrahydrofuran in a ratio of 1:1 mol. The reaction medium is stirred with a magnetic stirrer for 8-12 hours in an ice bath by adding dicyclohexylcarbodiimide (DCC) dissolved in tetrahydrofuran in a ratio of 1:1.25 mol. The DCC solution is added to the reaction medium at five-minute intervals for one hour. After the reaction is completed, it is kept at 2-4 °C overnight, and then the tetrahydrofuran is evaporated at low pressure after the DCU (dicyclohexyl urea) precipitated in the medium is removed by being filtered under vacuum. The obtained oily substance is solidified by taking it in an ice bath and adding cold diethyl ether onto it, and the formed solid substance, i.e. succinimide compounds (2), is dried by being filtered. In the step of synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102) of the inventive method (100), the succinimide compounds (2) are dissolved in tetrahydrofuran. Thiosemicarbazide dissolved in dimethyl sulfoxide (DMSO) is added onto it in a ratio of 1:1 mol and heated under a reflux cooler for 8-12 hours. After the reaction is finished, it is kept at 2-4 °C overnight. The tetrahydrofuran is evaporated at low pressure after the solid precipitated in the reaction medium is filtered. The product, i.e. thiosemicarbazide compounds (3), is precipitated by adding ice to the remaining part. In the step of synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103) of the inventive method (100), a 10% KOH is added onto the thiosemicarbazide compounds (3) and heated under a reflux cooler for 3-6 hours. The amount of KOH solution that will be added to the reaction medium is determined in such a way that a 20-25 mL KOH solution is added onto every 10 mmol of thiosemicarbazide compound. The solid portion that is not dissolved in the medium is removed by being filtered after the reaction is finished. The pH is adjusted to 4 by adding concentrated hydrochloric acid dropwise onto the filtrate in an ice bath. The precipitated product, i.e. 3-substituted-1,2,4- triazole-5-thione compounds (4-17), is washed with distilled water by being filtered under vacuum and purified by crystallization with ethanol after being dried. In the step of synthesizing 2-substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one compounds (4a-17z) from suitable triazole compounds (4-17) (104) of the inventive method (100), chloroacetic acid, anhydrous sodium acetate, concentrated acetic acid, acetic anhydride and substituted benzaldehyde are added onto the appropriate triazole compound (4-17) in a ratio of 1:1 mol and heated in an oil bath under a reflux cooler at 120-140 °C for 3-6 hours. The solid portion is removed by being filtered after the reaction is completed. The product crystallized from the medium, i.e. 2-Substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one compounds (4a-17z), is removed by being filtered and purified by crystallization in acetonitrile. The 2-substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one compounds (4a-17z) that can be obtained by the inventive method (100) are shown in Figure 3 and the spectral data of the synthesized compounds (4a-6z) are given below: (Z)-5-Benzylidene-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (4a) A yellow powder with a melting point of 178-179 °C. Yield 33,16%. IR spectrum: 3073 (C-H stretch, aromatic); 2925 (C-H stretch, aliphatic); 1728 (C=O stretch); 1598, 1579 (C=C stretch ve C=N stretch); 1131 (C-O stretch); peaks at 863, 843 (aromatic C-H bending) cm-1were observed.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,86 (6H, s, OCH3); 7,37 (2H, s, Ar.H); 7,56-7,62 (3H, m, Ar.H); 7,75 (2H, dd, J1=1,2 Hz, J2=8 Hz, Ar.H); 8,26 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 396,29 [M+H]+and 418,26 [M+Na]+. Analysis C20H17N3O4S; Calculated: 60,75 (C %); 4,33 (H %); 10,63 (N %); 8,11 (S %); Found: 60,43 (C %); 4,30 (H %); 10,76 (N %); 8,22 (S %). (Z)-5-(4-FloroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4b) A yellow powder with a melting point of 241-242 °C. Yield 58,60%. IR spectrum: 3073 (C-H stretch, aromatic); 2938 (C-H stretch, aliphatic); 1738 (C=O stretch); 1594, 1504, 1476 (C=C stretch and C=N stretch); 1163 (C-O stretch); 838, 802 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3), 3,85 (6H, s, OCH3), 7,33 (2H, s, Ar.H), 7,48 (2H, t, Ar.H); 7,65 (2H, dd, J1=5,2 Hz, J2=14 Hz, Ar.H); 8,23 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 414,31 [M+H]+and 436,23 [M+Na]+. Analysis C20H16FN3O4S; Calculated: 58,11 (C %); 3,90 (H %); 10,16 (N %); 7,75 (S %); Found: 58,31 (C %); 3,93 (H %); 9,89 (N %); 7,35 (S %). (Z)-5-(2-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (4c) A yellow powder with a melting point of 231-233 °C. Yield 65,02%. IR spectrum: 3020 (C-H stretch, aromatic); 2937 (C-H stretch, aliphatic); 1728 (C=O stretch); 1604, 1502 (C=C stretch and C=N stretch); 1125 (C-O stretch); 850, 836 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,86 (6H, s, OCH3); 7,34 (2H, s, Ar.H); 7,59 (2H, m, Ar.H); 7,70 (2H, m, Ar.H); 8,20 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 430,19 [M+H]+; 432,20 [M+H+2]+; 452,16 [M+Na]+and 454,16 [M+Na+2]+. Analysis C20H16ClN3O4S; Calculated: 55,88 (C %); 3,75 (H %); 9,78 (N %); 7,46 (S %); Found: 55,56 (C %); 3,82 (H %); 9,44 (N %); 7,38 (S %). (Z)-5-(4-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (4d) A yellow powder with a melting point of 212-213 °C. Yield 53,32%. IR spectrum: 2932 (C-H stretch, aliphatic); 1742 (C=O stretch); 1601, 1496 (C=C stretch and C=N stretch); 1136 (C-O stretch); 870, 842 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,85 (6H, s, OCH3); 7,36 (2H, s, Ar.H); 7,66 (2H, d, Ar.H); 7,76 (2H, d, Ar.H); 8,25 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 430,18 [M+H]+; 432,18 [M+H+2]+; 452,16 [M+Na]+and 454,15 [M+Na+2]+. Analysis C20H16ClN3O4S; Calculated: 55,88 (C %); 3,75 (H %); 9,78 (N %); 7,46 (S %); Found: 55,52 (C %); 3,69 (H %); 9,85 (N %); 7,11 (S %). (Z)-5-(4-NitroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4h) A yellow powder with a melting point of 228-229 °C. Yield 53,96%. IR spectrum: 3052 (C-H stretch, aromatic); 2939 (C-H stretch, aliphatic); 1724 (C=O stretch); 1583, 1509 (C=C stretch and C=N stretch); 1182 (C-O stretch); 845, 821 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,69 (3H, s, OCH3); 3,72 (6H, s, OCH3); 7,39 (2H, s, Ar.H); 7,80 (2H, d, Ar.H); 8,10 (1H, s, C=C-H); 8,20 (2H, d, Ar.H) ppm. Mass spectrum: (ESI), m / z 463,08 [M+Na]+. Analysis C20H16N4O6S; Calculated: 54,54 (C %); 3,66 (H %); 12,72 (N %); 7,28 (S %); Found: 54,26 (C %); 3,75 (H %); 12,83 (N %); 7,16 (S %). (Z)-5-(4-MethylBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4i) A yellow powder with a melting point of 180-181 °C. Yield 49,50%. IR spectrum: 3072 (C-H stretch, aromatic); 2931 (C-H stretch, aliphatic); 1736 (C=O stretch); 1612, 1581 (C=C stretch and C=N stretch); 1132 (C-O stretch); 847, 814 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,37 (3H, s, -CH3); 3,72 (3H, s, OCH3); 3,85 (6H, s, OCH3); 7,36 (2H, s, Ar.H); 7,41 (2H, d, Ar.H); 7,64 (2H, d, Ar.H); 8,21 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 410,25 [M+H]+and 432,22 [M+Na]+. Analysis C21H19N3O4S; Calculated: 61,60 (C %); 4,68 (H %); 10,26 (N %); 7,83 (S %); Found: 61,25 (C %); 4,69 (H %); 10,21 (N %); 7,76 (S %). (Z)-5-(2-Methoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4k) A yellow powder with a melting point of 202-203 °C. Yield 58,29%. IR spectrum: 3000 (C-H stretch, aromatic); 2938 (C-H stretch, aliphatic); 1743 (C=O stretch); 1589, 1499 (C=C stretch and C=N stretch); 1126 (C-O stretch); 846, 809 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,71 (3H, s, OCH3); 3,85 (6H, s, OCH3); 3,93 (3H, s, OCH3); 7,15 (1H, t, Ar.H); 7,20 (1H, d, Ar.H); 7,38 (2H, s, Ar.H); 7,55-7,59 (2H, m, Ar.H); 8,31 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 426,23 [M+H]+; 448,20 [M+Na]+. Analysis C21H19N3O5S; Calculated: 59,28 (C %); 4,50 (H %); 9,88 (N %); 7,54 (S %); Found: 58,73 (C %); 4,51 (H %); 9,76 (N %); 7,42 (S %). (Z)-5-(4-MethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4l) A yellow powder with a melting point of 183-184 °C. Yield 66,40%. IR spectrum: 3009 (C-H stretch, aromatic); 2995, 2939 (C-H stretch, aliphatic); 1724 (C=O stretch); 1583, 1509 (C=C stretch and C=N stretch); 1182 (C-O stretch); 845, 821 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,83 (3H, s, OCH3); 3,85 (6H, s, OCH3); 7,15 (2H, d, Ar.H); 7,35 (2H, s, Ar.H); 7,71 (2H, d, Ar.H); 8,20 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 426,22 [M+H]+; 448,19 [M+Na]+. Analysis C21H19N3O5S; Calculated: 59,28 (C %); 4,50 (H %); 9,88 (N %); 7,54 (S %); Found: 58,85 (C %); 4,55 (H %); 9,87 (N %); 7,47 (S %). (Z)-5-(2,3-DimethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4m) A yellow powder with a melting point of 207-209 °C. Yield: 71,50%. IR spectrum, 3056 (C-H stretch, aromatic); 2972 (C-H stretch, aliphatic); 1728 (C=O stretch); 1604, 1502 (C=C stretch and C=N stretch); 1359 (C-S stretch); 1125 (C-O stretch); 850, 836 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,84 (3H, s, OCH3); 3,85 (9H, s, OCH3); 7,19 (H, td, Ar.H); 7,28 (H, d, Ar.H); 7,30 (H, s, Ar.H ); 7,36 (2H, s, Ar.H); 8,27 (H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 456,23 [M+1]+and 478,30 [M+Na]+. Analysis C22H21N3O6S; Calculated: 58,01 (C %); 4,65 (H %); 9,23 (N %); 7,04 (S %); Found: 57,79 (C %); 4,63 (H %); 9,30 (N %); 7,06 (S %). (Z)-5-(2,5-DimethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4n) A yellow powder with a melting point of 231-232 °C. Yield: 60,44%. IR spectrum: 3046 (C-H stretch, aromatic); 2925 (C-H stretch, aliphatic); 1728 (C=O stretch); 1579, 1499 (C=C stretch and C=N stretch); 1368 (C-S stretch); 1130 (C-O stretch); 843, 800 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,74 (3H, s, OCH3); 3,80 (3H, s, OCH3); 3,88 (6H, s, OCH3); 3,90 (3H, s, OCH3); 7,11 (H, d, Ar.H); 7,18 (2H, d, Ar.H); 7,38 (2H, s, Ar.H); 8,29 (H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 456,15 [M+1]+ve 478,12 [M+Na]+. Analysis: C22H21N3O6S; Calculated: 58,01 (C %); 4,65 (H %); 9,23 (N %); 7,04 (S %); Found: 57,85 (C %); 4,62 (H %); 9,18 (N %); 7,02 (S %). (Z)-5-(3,4-Dimethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (4o) A yellow powder with a melting point of 220-221 °C. Yield: 62,15%. IR spectrum: 3122 (C-H stretch, aromatic); 2960, 2832 (C-H stretch, aliphatic); 1731 (C=O stretch); 1607, 1591, 1505 (C=C stretch ve C=N stretch); 1359 (C-S stretch); 1121 (C-O stretch); 941, 920 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,82 (3H, s, OCH3); 3,83 (3H, s, OCH3); 3,85 (6H, s, OCH3); 7,17 (H, d, Ar.H); 7,30 (H, d, Ar.H);7,34 (2H, s, Ar.H); 8,19 (H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 456,12 [M+1]+ve 478,20 [M+Na]+. Analysis C22H21N3O6S; Calculated: 58,01 (C %); 4,65 (H %); 9,23 (N %); 7,04 (S %); Found: 57,77 (C %); 4,63 (H %); 9,44 (N %); 7,03 (S %). (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (4p) A yellow powder with a melting point of 205-206 °C. Yield: 58,24%. IR spectrum: 3122 (C-H stretch, aromatic); 2942, 2843 (C-H stretch, aliphatic); 1736 (C=O stretch); 1587, 1480 (C=C stretch and C=N stretch); 1370 (C-S stretch); 1102 (C- O stretch); 893, 830 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,66 (3H, s, OCH3); 3,75 (6H, s, OCH3); 3,82 (3H, s, OCH3); 3,89 (6H, s, OCH3); 7,20 (2H, s, Ar.H); 7,32 (2H, s, Ar.H); 8,25 (H, s, C=C-H) ppm. Mass spectrum (ESI), m / z 486,08 [M+1]+and 508,21 [M+Na]+. Analysis: C23H23N3O7S; Calculated: 56,90 (C %); 4,78 (H %); 8,66 (N %); 6,60 (S %); Found: 56,85 (C %); 4,71 (H %); 8,62 (N %); 6,50 (S %). (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4t) A yellow powder with a melting point of 172-173 °C. Yield 59,41%. IR spectrum: 3002 (C-H stretch, aromatic); 2990, 2942 (C-H stretch, aliphatic); 1712 (C=O stretch); 1576, 1499 (C=C stretch and C=N stretch); 1130 (C-O stretch); 820, 817 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,72 (3H, s, OCH3); 3,83 (6H, s, OCH3); 7,35 (2H, s, Ar.H); 7,89 (1H, d, Ar.H); 7,95 (1H, d, Ar.H); 8,21 (1H, d, Ar.H); 8,28 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 520,93 [M+Na]+and 522,86 [M+Na+2]+. Analysis C21H15ClF3N3O4S; Calculated: 50,66 (C %); 3,04 (H %); 8,44 (N %); 6,44 (S %); Found: 50,85 (C %); 3,35 (H %); 8,72 (N %); 6,47 (S %). (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4z) An orange powder with a melting point of 192-193 °C. Yield 63,25%. IR spectrum: 3002 (C-H stretch, aromatic); 2991, 2936 (C-H stretch, aliphatic); 1723 (C=O stretch); 1590, 1502 (C=C stretch and C=N stretch); 1142 (C-O stretch); 830, 811 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,10 (6H, s, -N-CH3); 3,74 (3H, s, OCH3); 3,87 (6H, s, OCH3); 7,17 (1H, d, Ar.H); 7,35 (1H, s, Ar.H); 7,37 (2H, s, Ar.H); 7,62 (1H, d, Ar.H); 8,19 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 506,48 [M+Na]+. Analysis C22H21N5O6S; Calculated: 54,65 (C %); 4,38 (H %); 14,49 (N %); 6,63 (S %); Found: 54,52 (C %); 4,55 (H %); 14,22 (N %); 7,00 (S %). (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x1) A light brown powder with a melting point of 162-163 °C. Yield: 64,30%. IR spectrum: 3113 (C-H stretch, aromatic); 2991, 2939, 2835 (C-H stretch, aliphatic); 1734 (C=O stretch); 1613, 1594, 1546, 1496 (C=C and C=N stretch); 1359 (C-S stretch); 1140 (C-O stretch); 892, 841 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,74 (3H, s, OCH3); 3,87 (6H, s, OCH3); 6,85 (H, dd, J1: 3,6 Hz, J2: 2 Hz, Ar.H); 7,33 (H, d, J: 2 Hz, Ar. H); 7,36 (2H, s, Ar.H); 8,10 (H, s, C=C-H); 8,22 (H, d, J: 3,6 Hz, Ar. H) ppm. Mass spectrum (ESI), m / z 386,32 [M+1]+and 408,28 [M+Na]+. Analysis C18H15N3O5S; Calculated: 56,10 (C %); 3,92 (H %); 10,90 (N %); 8,32 (S %); Found: 56,06 (C %); 4,02 (H %); 10,99 (N %); 8,29 (S %). (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x2) A yellow powder with a melting point of 198-200 °C. Yield: 70%. IR spectrum: 3121 (C-H stretch, aromatic); 2942, 2837 (C-H stretch, aliphatic); 1717 (C=O stretch); 1591, 1451 (C=C stretch and C=N stretch); 1354 (C-S stretch); 1133 (C- O stretch); 830, 800 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,75 (3H, s, OCH3); 3,87 (6H, s, OCH3); 7,36 (2H, s, Ar.H); 7,41 (2H, dd, J1: 17,6 Hz, J2: 4 Hz, Ar.H); 7,60 (2H, d, Ar.H); 7,90 (2H, d, Ar.H); 8,10 (H, s, C=C-H) ppm. Mass spectrum (ESI), m / z 496,19 [M+1]+, 518,17 [M+Na]+and 520,17 [M+Na+2]+. Analysis C24H18ClN3O5S; Calculated: 58,13 (C %); 3,66 (H %); 8,47 (N %); 6,46 (S %); Found: 58,02 (C %); 4,02 (H %); 8,17 (N %); 5,97 (S %). (Z)-5-[5-(2,5-(5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (4x3) A brown powder with a melting point of 187-188 °C. Yield: 61,64%. IR spectrum: 3129 (C-H stretch, aromatic); 2994, 2932, 2828 (C-H stretch, aliphatic); 1728 (C=O stretch); 1603, 1546 (C=C stretch and C=N stretch); 1356 (C-S stretch); 1124 (C- O stretch); 893, 857 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,75 (3H, s, OCH3); 3,87 (6H, s, OCH3); 7,38 (2H, s, Ar.H); 7,48 (H, d, Ar.H); 7,52 (H, d, Ar.H); 7,55 (H, d, Ar.H); 7,67 (H, d, Ar.H); 7,92 (H, d, Ar.H); 8,16 (H, s, C=C- H) ppm. Mass spectrum (ESI), m / z 530,16 [M+1]+, 552,19 [M+Na]+and 554,19 Hz, Ar.H); 8,00 (H, dd, J1: 8 Hz, J2: 1,2 Hz, Ar.H); 8,06 (H, dd, J1: 8 Hz, J2: 1,2 Hz, Ar.H); 8,12 (H, s, C=C-H) ppm. Mass spectrum (ESI), m / z 529,19 [M+Na]+. Analysis C24H18N4O7S; Calculated: 56,91 (C %); 3,58 (H %); 11,06 (N %); 6,33 (S %); Found: 56,50 (C %); 3,74 (H %); 11,19 (N %); 6,24 (S %). An orange powder with a melting point of 222-223 °C. Yield: 78,16%. IR spectrum: 3120 (C-H stretch, aromatic); 2837 (C-H stretch, aliphatic); 1720 (C=O stretch); 1666, 1596 (C=C stretch and C=N stretch); 1329 (C-S stretch); 1133 (C-O stretch); 921, 897 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,75 (3H, s, OCH3); 3,86 (6H, s, OCH3); 7,31 (2H, s, Arom. H.); 7,54 (H, d, Ar.H); 7,67 (H, d, Ar.H); 8,10 (2H, d, Ar.H); 8,32 (2H, d, Ar.H); 8,25 (H, s, C=C-H) ppm. Mass spectrum (ESI), m / z 529,18 [M+Na]+. Analysis; Calculated: 56,91 (C %); 3,58 (H %); 11,06 (N %); 6,33 (S %); Found: 56,71 (C %); 3,92 (H %); 10,89 (N %); 6,15 (S %). (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x7) A brown powder with a melting point of 171-172 °C. Yield: 63,60%. IR spectrum: 3001 (C-H stretch, aromatic); 2981, 2929, 2829 (C-H stretch, aliphatic); 1744 (C=O stretch); 1592, 1508 (C=C stretch and C=N stretch); 1377 (C-S stretch); 1125 (C- O stretch); 843, 814 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,81 (3H, s, C-CH3) 3,71 (3H, s, OCH3); 3,88 (6H, s, OCH3); 7,26 (2H, s, Arom. H.); 7,39-7,48 (2H, m, Ar.H); 8,03 (H, d, Ar.H); 8,11 (H, s, C=C-H); 8,36 (H, d, Ar.H); 8,39 (H, s, Ar.H) ppm. Mass spectrum (ESI), m / z 499,35 [M+Na]+. Analysis C24H20N4O5S; Calculated: 60,50 (C %); 4,23 (H %); 11,76 (N %); 6,73 (S %); Found: 60,68 (C %); 4,35 (H %); 11,52 (N %); 6,70 (S %). (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x8) A brown powder with a melting point of 180-181 °C. Yield: 68,70%. IR spectrum: 3069 (C-H stretch, aromatic); 2932, 2835 (C-H stretch, aliphatic); 1737 (C=O stretch); 1591, 1505 (C=C stretch and C=N stretch); 1372 (C-S stretch); 1133 (C- O stretch); 855, 845 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,62 (3H, s, N-CH3), 3,77 (3H, s, OCH3); 3,85 (6H, s, OCH3); 7,31 (2H, s, Arom. H.); 7,39-7,48 (2H, m, Ar.H); 7,59 (H, d, Ar.H); 8,02 (H, d, Ar.H); 8,14 (H, s, C=C-H); 8,44 (H, s, Ar.H) ppm. Mass spectrum (ESI), m / z 449,10 [M+1]+ve 471,13 [M+Na]+. Analysis C23H20N4O4S; Calculated: 61,60 (C %); 4,50 (H %); 12,49 (N %); 7,15 (S %); Found: 61,18 (C %); 4,32 (H %); 12,35 (N %); 7,11 (S %). (Z)-5-Benzylidene-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (5a) A yellow powder with a melting point of 190-192 °C. Yield 39,11%. IR spectrum: 3004 (C-H stretch, aromatic); 2941 (C-H stretch, aliphatic); 1750 (C=O stretch); 1642, 1593, 1514 (C=C stretch and C=N stretch); 1138 (C-O stretch); 883, 815 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,69 (3H, s, OCH3); 3,73 (6H, s, OCH3); 4,02 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,53-7,60 (3H, m, Ar.H); 7,73 (2H, d, Ar.H); 8,12 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 432,38 [M+Na]+. Analysis C21H19N3O4S; Calculated: 61,60 (C %); 4,68 (H %); 10,26 (N %); 7,83 (S %); Found: 61,79 (C %); 4,89 (H %); 10,39 (N %); 7,97 (S %). (Z)-5-(4-Fluorobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5b) A yellow powder with a melting point of 246-247 °C. Yield 78,60%. IR spectrum: 3008 (C-H stretch, aromatic); 2941, 2933 (C-H stretch, aliphatic); 1710 (C=O stretch); 1636, 1560,1512 (C=C stretch and C=N stretch); 1131 (C-O stretch); 840, 822 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,60 (3H, s, OCH3); 3,73 (6H, s, OCH3); 4,02 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,43 (2H, t, Ar.H); 7,80 (2H, dd, J1:5,2 Hz, J2:14 Hz, Ar.H); 8,24 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 450,29 [M+Na]+. Analysis C21H18FN3O4S; Calculated: 59,01 (C %); 4,24 (H %); 9,83 (N %); 7,50 (S %); Found: 58,86 (C %); 4,34 (H %); 9,93 (N %); 7,59 (S %). (Z)-5-(2-ChloroBenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5c) A yellow powder with a melting point of 170-171 °C. Yield 75,38%. IR spectrum: 3004 (C-H stretch, aromatic); 2948 (C-H stretch, aliphatic); 1728 (C=O stretch); 1626, 1585,1506 (C=C stretch and C=N stretch); 1129 (C-O stretch); 866, 850 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,61 (3H, s, OCH3); 3,73 (6H, s, OCH3); 4,03 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,55-7,71 (4H, m, Ar. H); 8,27 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 466,31 [M+Na]+and 468,31 [M+Na+2]+. Analysis C21H18ClN3O4S; Calculated: 56,82 (C %); 4,09 (H %); 9,47 (N %); 7,22 (S %); Found: 56,65 (C %); 4,25 (H %); 9,71 (N %); 7,29 (S %). (Z)-5-(4-ChloroBenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5d) A yellow powder with a melting point of 178-179 °C. Yield 65,63%. IR spectrum: 3008 (C-H stretch, aromatic); 2934 (C-H stretch, aliphatic); 1750 (C=O stretch); 1626, 1585, 1508 (C=C stretch and C=N stretch); 1138 (C-O stretch); 870, 853 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,61 (3H, s, OCH3); 3,73 (6H, s, OCH3); 4,03 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,65 (2H, m, Ar. H); 7,76 (2H, d, Ar.H); 8,22 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 466,93 [M+Na]+and 468,94 [M+Na+2]+. Analysis C21H18ClN3O4S; Calculated: 56,82 (C %); 4,09 (H %); 9,47 (N %); 7,22 (S %); Found: 56,42 (C %); 4,16 (H %); 9,69 (N %); 7,30 (S %). (Z)-5-(4-Nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (5h) A brown powder with a melting point of 191-192 °C. Yield 71,64%. IR spectrum: 3066 (C-H stretch, aromatic); 2941 (C-H stretch, aliphatic); 1749 (C=O stretch); 1612, 1581, 1504 (C=C stretch and C=N stretch); 1121 (C-O stretch); 832, 815 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,60 (3H, s, OCH3); 3,72 (6H, s, OCH3); 4,03 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,98 (2H, d, Ar.H); 8,32 (1H, s, C=C-H); 8,36 (2H, d, Ar.H) ppm. Mass spectrum (ESI): m / z 477,29 [M+Na]+. Analysis C21H18N4O6S; Calculated: 55,50 (C %); 3,99 (H %); 12,33 (N %); 7,05 (S %); Found: 55,97 (C %); 4,08 (H %); 12,49 (N %); 7,25 (S %). (Z)-5-(4-Methylbenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5i) A yellow powder with a melting point of 187-189 °C. Yield 70,26%. IR spectrum: 3004 (C-H stretch, aromatic); 2934 (C-H stretch, aliphatic); 1728 (C=O stretch); 1620, 1585, 1542 (C=C stretch and C=N stretch); 1138 (C-O stretch); 870, 853 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,36 (3H, s, -CH3); 3,60 (3H, s, OCH3); 3,72 (6H, s, OCH3); 4,02 (2H, s, -CH2-); 6,61 (2H, s, Ar.H); 7,39 (2H, d, Ar. H); 7,62 (2H, d, Ar.H); 8,17 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 446,31 [M+Na]+. Analysis C22H21N3O4S; Calculated: 62,40 (C %); 5,00 (H %); 9,92 (N %); 7,57 (S %); Found: 62,35 (C %); 5,23 (H %); 9,96 (N %); 7,57 (S %). (Z)-5-(2-MethoxyBenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5k) A yellow powder with a melting point of 186-187 °C. Yield 83,50%. IR spectrum: 3001 (C-H stretch, aromatic); 2942 (C-H stretch, aliphatic); 1732 (C=O stretch); 1602, 1588, 1511 (C=C stretch and C=N stretch); 1125 (C-O stretch); 840, 813 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,60 (3H, s, OCH3); 3,72 (6H, s, OCH3); 3,91 (3H, s, OCH3); 4,01 (2H, s, -CH2-), 6,61 (2H, s, Ar.H); 7,13 (1H, t, Ar.H); 7,19 (1H, d, Ar.H); 7,53 (1H, d, Ar.H); 7,55 (1H, t, Ar.H); 8,28 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 462,29 [M+Na]+. Analysis C22H21N3O5S; Calculated: 60,13 (C %); 4,82 (H %); 9,56 (N %); 7,29 (S %); Found: 59,88 (C %); 5,06 (H %); 9,63 (N %); 7,33 (S %). (Z)-5-(4-Methoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5l) A yellow powder with a melting point of 195-196 °C. Yield 80,03%. IR spectrum: 3012 (C-H stretch, aromatic); 2942 (C-H stretch, aliphatic); 1732 (C=O stretch); 1607, 1595, 1505 (C=C stretch and C=N stretch); 1125 (C-O stretch); 840, 813 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,60 (3H, s, OCH3); 3,72 (6H, s, OCH3); 3,82 (3H, s, OCH3); 4,02 (2H, s, -CH2-); 6,62 (2H, s, Ar.H); 7,17 (2H, d, Ar. H); 7,33 (2H, d, Ar.H); 8,16 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 462,28 [M+Na]+. Analysis C22H21N3O5S; Calculated: 60,13 (C %); 4,82 (H %); 9,56 (N %); 7,29 (S %); Found: 59,84 (C %); 5,04 (H %); 9,54 (N %); 7,34 (S %). (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5t) A yellow powder with a melting point of 172-173 °C. Yield 82,10%. IR spectrum: 3000 (C-H stretch, aromatic); 2991, 2910 (C-H stretch, aliphatic); 1723 (C=O stretch); 1589, 1476 (C=C stretch and C=N stretch); 1103 (C-O stretch); 875, 830 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,61 (3H, s, OCH3); 3,73 (6H, s, OCH3); 4,03 (2H, s, -CH2-), 6,62 (2H, s, Ar.H); 7,92 (1H, d, Ar.H); 7,97 (1H, d, Ar.H); 8,24 (1H, d, Ar.H); 8,33 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 512,14 [M+H]+, 534,11 [M+Na]+ve 536,08 [M+Na+2]+. Analysis C22H17ClF3N3O4S; Calculated: 51,62 (C %); 3,35 (H %); 8,21 (N %); 6,26 (S %); Found: 51,75 (C %); 3,42 (H %); 8,51 (N %); 6,47 (S %). (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5z) An orange powder with a melting point of 183-184 °C. Yield 75,88%. IR spectrum: 3022 (C-H stretch, aromatic); 2993, 2932 (C-H stretch, aliphatic); 1752 (C=O stretch); 1570, 1492 (C=C stretch and C=N stretch); 1169 (C-O stretch); 810, 847 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 3,10 (6H, s, -N-CH3); 3,74 (3H, s, OCH3); 3,87 (6H, s, OCH3); 4,02 (2H, s, -CH2-); 6,60 (2H, s, Ar.H); 7,12 (1H, dd, J1:2,8 Hz, J2:8,8 Hz, Ar.H); 7,34 (1H, d, J:2,8 Hz, Ar.H); 7,59 (1H, d, J:8,8 Hz, Ar.H); 8,19 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 498,22 [M+H]+and 520,20 [M+Na]+peaks were observed. Analysis C23H23N5O6S; Calculated: 55,53 (C %); 4,66 (H %); 14,08 (N %); 6,64 (S %); Found: 55,59 (C %); 4,81 (H %); 14,05 (N %); 6,53 (S %). (Z)-5-Benzylidene-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (6a) A yellow powder with a melting point of 149-150 °C. Yield 72,65%. IR spectrum: 3001 (C-H stretch, aromatic); 2981, 2929 (C-H stretch, aliphatic); 1744 (C=O stretch); 1611, 1592, 1508 (C=C stretch and C=N stretch); 1125 (C-O stretch); 843, 814 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,96 (2H, t, Ar-CH2- CH2); 3,04 (2H, t, Ar-CH2-); 3,59 (3H, s, OCH3); 3,73 (6H, s, OCH3), 6,57 (2H, s, Ar.H); 7,55-7,60 (3H, m, Ar. H); 7,74 (2H, d, Ar.H); 8,21 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 446,24 [M+Na]+. Analysis C22H21N3O4S; Calculated: 62,40 (C %); 5,00 (H %); 9,92 (N %); 7,57 (S %); Found: 62,18 (C %); 5,21 (H %); 9,94 (N %); 7,53 (S %). (Z)-5-(4-Fluorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6b) A yellow powder with a melting point of 162-163 °C. Yield 68,26%. IR spectrum: 3059 (C-H stretch, aromatic); 2941 (C-H stretch, aliphatic); 1736 (C=O stretch); 1587, 1520, 1470 (C=C stretch and C=N stretch); 1122 (C-O stretch); 893, 856 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,98 (2H, t, Ar-CH2-CH2); 3,04 (2H, t, Ar-CH2-); 3,59 (3H, s, OCH3); 3,72 (6H, s, OCH3); 6,57 (2H, s, Ar.H); 7,43 (2H, t, Ar. H); 7,81 (2H, dd, J1:5,2 Hz, J2:14 Hz, Ar.H); 8,23 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 464,21 [M+Na]+. Analysis C22H20FN3O4S; Calculated: 59,85 (C %); 4,57 (H %); 9,52 (N %); 7,26 (S %); Found: 59,98 (C %); 4,79 (H %); 9,63 (N %); 7,32 (S %). (Z)-5-(2-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6c) A yellow powder with a melting point of 142-143 °C. Yield 73,50%. IR spectrum: 3002 (C-H stretch, aromatic); 2931 (C-H stretch, aliphatic); 1744 (C=O stretch); 1612, 1591, 1509 (C=C stretch and C=N stretch); 1130 (C-O stretch); 891, 843 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,98 (2H, t, Ar-CH2-CH2); 3,07 (2H, t, Ar-CH2-); 3,61 (3H, s, OCH3); 3,74 (6H, s, OCH3); 6,58 (2H, s, Ar.H); 7,56-7,61 (2H, m, Ar. H); 7,68-7,73 (2H, m, Ar.H); 8,28 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 480,16 [M+Na]+ve 482,20 [M+Na+2]+. Analysis C22H20ClN3O4S; Calculated: 57,70 (C %); 4,40 (H %); 9,18 (N %); 7,00 (S %); Found: 57,32 (C %); 4,54 (H %); 9,36 (N %); 7,00 (S %). (Z)-5-(4-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6d) A yellow powder with a melting point of 162-163 °C. Yield 80,31%. IR spectrum: 3008 (C-H stretch, aromatic); 2936 (C-H stretch, aliphatic); 1741 (C=O stretch); 1613, 1588, 1505 (C=C stretch and C=N stretch); 1198 (C-O stretch); 822, 813 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,97 (2H, t, Ar-CH2-CH2); 3,04 (2H, t, Ar-CH2-); 3,63 (3H, s, OCH3); 3,75 (6H, s, OC H3); 6,61 (2H, s, Ar.H); 7,49 (2H, d, Ar. H); 7,62 (2H, d, Ar.H); 8,23 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 480,16 [M+Na]+ve 482,16 [M+Na+2]+. Analysis C22H20ClN3O4S; Calculated: 57,70 (C %); 4,40 (H %); 9,18 (N %); 7,00 (S %); Found: 57,48 (C %); 4,48 (H %); 9,40 (N %); 6,46 (S %). (Z)-5-(4-Nitrobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (6h) A brown powder with a melting point of 174-175 °C. Yield 76,18%. IR spectrum: 3069 (C-H stretch, aromatic); 2932 (C-H stretch, aliphatic); 1737 (C=O stretch); 1617, 1591, 1505 (C=C stretch and C=N stretch); 1133 (C-O stretch); 855, 845 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,96 (2H, t, Ar-CH2-CH2); 3,05 (2H, t, Ar-CH2-); 3,59 (3H, s, OCH3); 3,73 (6H, s, OCH3); 6,57 (2H, s, Ar.H); 7,97 (2H, d, Ar. H); 8,32 (1H, s, C=C-H); 8,37 (2H, d, Ar.H) ppm. Mass spectrum (ESI): m / z 491,18 [M+Na]+. Analysis C22H20N4O6S; Calculated: 56,40 (C %); 4,30 (H %); 11,96 (N %); 6,84 (S %); Found: 56,23 (C %); 4,47 (H %); 11,98 (N %); 6,86 (S %). (Z)-5-(4-Methylbenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6i) A yellow powder with a melting point of 163-164 °C. Yield 81,36%. IR spectrum: 3020 (C-H stretch, aromatic); 2930 (C-H stretch, aliphatic); 1744 (C=O stretch); 1612, 1592, 1509 (C=C stretch and C=N stretch); 1123 (C-O stretch); 843, 815 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,37 (3H, s, -CH3); 2,97 (2H, t, Ar-CH2-CH2); 3,04 (2H, t, Ar-CH2-); 3,59 (3H, s, OCH3); 3,73 (6H, s, OCH3); 6,57 (2H, s, Ar.H); 7,39 (2H, d, Ar. H); 7,63 (2H, d, Ar.H); 8,17 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 460,23 [M+Na]+. Analysis C23H23N3O4S; Calculated: 63,14 (C %); 5,30 (H %); 9,60 (N %); 7,33 (S %); Found: 63,26 (C %); 5,18 (H %); 9,74 (N %); 7,36 (S %). (Z)-5-(2-Methoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (6k) A yellow powder with a melting point of 152-153 °C. Yield 75,64%. IR spectrum: 3007 (C-H stretch, aromatic); 2935 (C-H stretch, aliphatic); 1739 (C=O stretch); 1622, 1590, 1505 (C=C stretch and C=N stretch); 1130 (C-O stretch); 845, 823 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,98 (2H, t, Ar-CH2-CH2); 3,05 (2H, t, Ar-CH2-); 3,61 (3H, s, OCH3); 3,74 (6H, s, OCH3); 3,93 (3H, s, OCH3); 6,57 (2H, s, Ar.H); 7,14 (1H, t, Ar.H); 7,20 (1H, d, Ar.H); 7,56 (2H, m, Ar.H); 8,30 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 476,22 [M+Na]+. Analysis C23H23N3O5S; Calculated: 60,91 (C %); 5,11 (H %); 9,27 (N %); 7,07 (S %); Found: 60,50 (C %); 5,35 (H %); 9,34 (N %); 7,07 (S %). (Z)-5-(4-Methoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (6l) A yellow powder with a melting point of 204-205 °C. Yield 79,33%. IR spectrum: 3003 (C-H stretch, aromatic); 2936 (C-H stretch, aliphatic); 1745 (C=O stretch); 1601, 1580, 1516 (C=C stretch and C=N stretch); 1136 (C-O stretch); 843, 820 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,97 (2H, t, Ar-CH2-CH2); 3,04 (2H, t, Ar-CH2-); 3,59 (3H, s, OCH3); 3,73 (6H, s, OCH3); 3,84 (3H, s, OCH3); 6,56 (2H, s, Ar.H); 7,14 (2H, d, Ar.H); 7,72 (2H, d, Ar.H); 8,18 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 476,22 [M+Na]+. Analysis C23H23N3O5S; Calculated: 60,91 (C %); 5,11 (H %); 9,27 (N %); 7,07 (S %); Found: 60,79 (C %); 5,35 (H %); 9,34 (N %); 7,07 (S %). (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6t) A yellow powder with a melting point of 179-180 °C. Yield 79,63%. IR spectrum: 3086 (C-H stretch, aromatic); 2995, 2929 (C-H stretch, aliphatic); 1703 (C=O stretch); 1569, 1471 (C=C stretch and C=N stretch); 1162 (C-O stretch); 893, 852 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,99 (2H, t, Ar-CH2-CH2); 3,06 (2H, t, Ar-CH2-); 3,61 (3H, s, OCH3); 3,75 (6H, s, OCH3); 6,59 (2H, s, Ar.H); 7,99 (2H, d, Ar.H); 8,30 (1H, s, C=C-H); 8,46 (1H, d, Ar.H) ppm. Mass spectrum (ESI): m / z 526,16 [M+H]+ve 548,12 [M+Na]+ve 550,15 [M+Na+2]+. C23H19ClF3N3O4S; Calculated: 52,53 (C %); 3,64 (H %); 7,99 (N %); 6,10 (S %); Found: 52,45 (C %); 3,84 (H %); 8,12 (N %); 6,29 (S %). (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6z) An orange powder with a melting point of 175-176°C. Yield 81,50%. IR spectrum: 3002 (C-H stretch, aromatic); 2990, 2942 (C-H stretch, aliphatic); 1712 (C=O stretch); 1576, 1499 (C=C stretch and C=N stretch); 1130 (C-O stretch); 820, 817 (Aromatic C-H bending) cm-1.1H-NMR (DMSO-d6) δ: 2,98 (2H, t, Ar-CH2-CH2); 3,06 (2H, t, Ar-CH2-); 3,11 (6H, s, -N-CH3); 3,61 (3H, s, OCH3); 3,75 (6H, s, OCH3); 6,58 (2H, s, Ar.H); 7,16 (1H, dd, J1:2,8 Hz, J2:8,8 Hz, Ar.H); 7,37 (1H, d, J:2,8 Hz, Ar.H); 7,63 (1H, d, J:8,8 Hz, Ar.H); 8,18 (1H, s, C=C-H) ppm. Mass spectrum (ESI): m / z 512,24 [M+H]+ve 534,21 [M+Na]+. Analysis C24H25N5O6S; Calculated: 56,35 (C %); 4,93 (H %); 13,69 (N %); 6,27 (S %); Found: 56,42 (C %); 4,88 (H %); 13,79 (N %); 6,45 (S %). In silico computer-aided drug design studies were carried out for the compounds obtained by the inventive method (100). The synthesized compounds were drawn in two dimensions by using ChemDraw 2D (version 16.0) software and then three- dimensional models were obtained by transferring them to ChemDraw 3D (version 16.0) software. MM2 forcefield module of ChemDraw 3D software was used in energy minimization of ligands. The protein coded 1M17 was selected from the Protein Data Bank (www.rcsb.org) with the aim of performing docking studies on Epidermal Growth Factor Receptor (EGFR). This protein is the ATP binding site of the EGFR receptor and consists of a single chain. The binding site of the protein contains the erlotinib inhibitor. As part of the protein preparation process, water molecules more than 5 Å away from the ligand in the binding site were removed by using BioVia Discovery Studio (version 4) software. In Autodock Tools (version 1.5.6) software, polar proteins were first added to the structure and then Kollman charges were assigned. Molecular docking studies were carried out by using Autodock Vina software. For the docking process with Autodock Vina, the AutoDockTools interface was used. The central coordinates of erlotinib (22,04; - 0,31; 53,57) located in the active site of the protein were used as the center of the docking search space and grid maps were created based on these coordinates. In the docking studies, firstly, the docking process was performed again by removing erlotinib in the active pocket of the protein from the active pocket for the validation of the protocols and the RMSD value of the compound was found to be 0,89 A. The binding energy of erlotinib in the receptor was found to be -7,2 kcal / mol after docking studies. When the binding pattern in the active pocket is examined, it was observed that erlotinib showed hydrophobic interactions with Leu694, Ala719, Lys721, Leu764, Gln767 and Leu820 amino acids and formed a hydrogen bond with Met769 amino acid. It is indicated in the literature that the hydrogen bond formed by Erlotinib with Met769 is an important interaction for EGFR inhibition activity. In the in silico studies that prepared the ground for the study, firstly, the volumetric and 3-dimensional topological similarities of the synthesized compounds with the active substances, which are known to be EGFR inhibitors and have commercially available preparations, were studied with Openeye vROCS software. In the similarity screening, erlotinib, canertinib, dacomitinib, afatinib, gefitinib, lapatinib, neratinib, pelitinib and vandetanib, which are known to be EGFR inhibitors and have commercially available preparations, were selected as target compounds. In the examination of the results, the evaluation lower limit for the similarity ratio was determined as 0,7. It was determined that a significant portion of the compounds that were designed accordingly showed a considerable topological similarity with the erlotinib, afatinib and vandetanib active substances. Then, docking studies of the compounds with the ATP binding site of the EGFR protein were carried out in order to detect potential binding modes and binding energies. After carrying out the redocking of erlotinib, docking studies of the synthesized compounds with EGFR protein were performed and the binding energies of the compounds were found to be -7.0 to -8,6 kcal / mol. When the interactions of the compounds with amino acids in the poses obtained after docking studies were examined; it was observed that the majority of the compounds formed hydrogen bonds with the amino acid Met769, which plays a key role for EGFR inhibition. Apart from this, hydrophobic interactions with the amino acids Leu694, Ala719, Lys721, Leu764, Gln767 and Leu820 were also observed. In conclusion, the fact that the designed compounds have a good binding energy, exhibit similar binding properties (showing interaction with similar amino acids) with erlotinib and exhibit topological similarity to various EGFR inhibitors supports the hypothesis that our compounds are potential EGFR inhibitors. On the basis of these results, EGFR inhibition activities of the compounds were evaluated by western blot and in vitro enzyme assays. In addition, biological activity studies were performed for the compounds obtained by the inventive method (100). In order to examine the effect of the designed compounds on EGFR activity, the EGFR inhibition activities of the compounds were evaluated by applying Western Blot test in the A549 cell line to two compounds (6z and 6t) selected by evaluating in silico study results and preliminary cytotoxicity studies. The growth curves of the compounds in the A549 cell line were generated with the aim of determining the test dose and the doses of 50 µM and 100 µM, which inhibited the growth the most, were determined as the test dose for both compounds. After this study, it was revealed that a 100 µM dose of 6z (Figure-4) compound and a 50 µM dose of 6t (Figure-5) compound led to inhibition on EGFR; and that 6z compound exhibited higher activity than 6t compound. After demonstrating the potential EGFR inhibition activity of the compounds, in vitro enzyme tests were carried out with some of the compounds in order to prove whether the activity originated from EGFR or not, and the IC50 values of the compounds are given in Figure-6. When the results are examined, it is seen that the tested compounds inhibit EGFR at nM and µM levels. The said findings are in accordance with western blot test results and in silico studies. Based on all these experimental findings, it is confirmed that the designed compounds are potential EGFR inhibitors. Within these basic concepts; it is possible to develop various embodiments of the inventive “Compounds for Inhibiting EGFR and Synthesis Method (100) of the Compounds”; the invention cannot be limited to examples disclosed herein and it is essentially according to claims.

Claims

CLAIMS 1. Compounds (4a-17z) which have formula (I)1that enables EGFR inhibition, which is involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition; and is characterized as 2-substituted-5-arylidenethiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one derivative.

2. Compounds according to Claim 1; characterized by compounds of formula (I): (Z)-5-Benzylidene-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4a), (Z)-5-(4-FloroBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4b), (Z)-5-(2- Chlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (4c), (Z)-5-(4-Chlorobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (4d), (Z)-5-(2,4- Dichlorobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (4e), (Z)-5-(4-Bromobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4f), (Z)-5-(3- NitroBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (4g), (Z)-5-(4-NitroBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4h), (Z)-5-(4- MethylBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4i), (Z)-5-(4-Trifluoromethylbenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (4j), (Z)-5-(2- Methoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (4k), (Z)-5-(4-MethoxyBenzylidene)-2-(3,4,5- 2trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4l), (Z)-5-(2,3- DimethoxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4m), (Z)-5-(2,5-DimethoxyBenzylidene)-2- (3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4n), (Z)- 5-(3,4-Dimethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (4o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2- (3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (4p), (Z)- 5-(2-Bromo-5-methoxybenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (4r), (Z)-5-(4- Trifluoromethoxybenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (4s), (Z)-5-(4-Chloro-3- trifluoromethylbenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (4t), (Z)-5-(2-Chloro-5-nitrobenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4u), (Z)-5-(4- Chloro-3-nitrobenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (4v), (Z)-5-(4-DimethylamineBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4y), (Z)-5-(4- Dimethylamine-2-nitroBenzylidene)-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (4z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (4x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il- Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)- one (4x2), (Z)-5-[5-(2,5-(5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (4x3), (Z)-5-[5- (3,4-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2- 3b][1,2,4]triazol-6(5H)-one (4x7), (Z)-5-[(1-Methyl)-1H-indol-3-il- Methylen]-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)- one (4x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5- trimethoxyphenyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (4x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-(3,4,5-trimethoxyphenyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (4x10), (Z)-5-Benzylidene-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5a), (Z)-5-(4- Fluorobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5b), (Z)-5-(2-ChloroBenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5c), (Z)-5-(4- ChloroBenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5e), (Z)-5-(4- Bromobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (5f), (Z)-5-(3-Nitrobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (5g), (Z)-5-(4- Nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (5h), (Z)-5-(4-Methylbenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5j), (Z)-5-(2-MethoxyBenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5k), (Z)-5-(4- Methoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (5l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (5m), (Z)-5- (2,5-Dimethoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5n), (Z)-5-(3,4-DimethoxyBenzylidene)-2- (3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5o), (Z)- 5-(3,4,5-Trimethoxybenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (5p), (Z)-5-(2-Bromo-5-methoxybenzylidene)- 2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (5r), 4(Z)-5-(4-Trifluoromethoxybenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (5s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5t), (Z)-5-(2- Chloro-5-nitroBenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5v), (Z)-5-(4- Dimethylaminebenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)- 2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (5z), (Z)- 5-[5-Phenylfuran-2-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il- Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)- one (5x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x3), (Z)-5-[5- (3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x6), 5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (5x7), (Z)-5-[(1-Methyl)-1H-indol-3-il- Methylen]-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)- one (5x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5- triMethoxybenzyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (5x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-(3,4,5-triMethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (5x10), (Z)-5-Benzylidene-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6a), (Z)-5-(4- Fluorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6b), (Z)-5-(2-Chlorobenzylidene)-2-(3,4,5- 5trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6c), (Z)-5- (4-Chlorobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (6d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4,5- trimethoxybenzyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6e), (Z)-5-(4- BromoBenzylidene)-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (6f), (Z)-5-(3-NitroBenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6g), (Z)-5-(4- Nitrobenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (6h), (Z)-5-(4-Methylbenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6i), (Z)-5- (4-Trifluoromethylbenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2- b]-1,2,4-triazole-6(5H)-one (6j), (Z)-5-(2-Methoxybenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6k), (Z)-5- (4-Methoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (6l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (6m), (Z)-5- (2,5-Dimethoxybenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (6n), (Z)-5-(3,4-Dimethoxybenzylidene)-2- (3,4,5-trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6o), (Z)-5-(3,4,5-TriMethoxyBenzylidene)-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6p), (Z)-5-(2- Bromo-5-MethoxyBenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (6r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2- (3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (6t), (Z)-5- (2-Chloro-5-nitrobenzylidene)-2-(3,4,5-trimethoxybenzyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (6u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6v), (Z)-5-(4- Dimethylaminebenzylidene)-2-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (6y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)- 62-(3,4,5-trimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (6z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x1), (Z)-5-[5- (4-Chlorophenyl)furan-2-il-Methylen]-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (6x2), (Z)-5- [5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4,5- trimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x3), (Z)-5- [5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x6), (Z)-5- [(1-Acetyl)-1H-indol-3-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x8), (Z)-5- [(2-Methyl)-1H-indol-3-il-Methylen]-2-(3,4,5- triMethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (6x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-(3,4,5-triMethoxyfenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (6x10), (Z)-5-Benzylidene-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7a), (Z)-5-(4- Fluorobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (7b), (Z)-5-(2-Chlorobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7c), (Z)-5- (4-Chlorobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (7d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7e), (Z)-5- (4-Bromobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (7f), (Z)-5-(3-Nitrobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7g), (Z)-5- 7(4-Nitrobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (7h), (Z)-5-(4-MethylBenzylidene)-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (7j), (Z)-5-(2-Methoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7k), (Z)-5- (4-Methoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (7l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (7m), (Z)-5- (2,5-Dimethoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (7n), Z)-5-(3,4-Dimethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (7o), (Z)-5- (3,4,5-Trimethoxybenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (7p), (Z)-5-(2-Bromo-5-methoxybenzylidene)- 2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (7r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7t), (Z)-5-(2- Chloro-5-nitrobenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (7u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7v), (Z)-5-(4- Dimethylaminebenzylidene)-2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (7y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)- 2-(2,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (7z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x1), (Z)-5-[5- (4-Chlorophenyl)furan-2-il-Methylen]-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (7x2), (Z)-5- [5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(2,5- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x3), (Z)-5- 8[5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x6), (Z)-5- [(1-Acetyl)-1H-indol-3-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x8), (Z)-5- [(2-Methyl)-1H-indol-3-il-Methylen]-2-(2,5- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (7x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-(2,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (7x10), (Z)-5-Benzylidene-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8a), (Z)-5- (4-Fluorobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (8b), (Z)-5-(2-Chlorobenzylidene)-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8c), (Z)-5-(4- ChloroBenzylidene)-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (8d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8e), (Z)-5- (4-Bromobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (8f), (Z)-5-(3-Nitrobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8g), (Z)-5- (4-Nitrobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (8h), (Z)-5-(4-MethylBenzylidene)-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (8j), (Z)-5-(2-Methoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8k), (Z)-5-(4- Methoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4- 9triazole-6(5H)-one (8l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (8m), (Z)-5- (2,5-Dimethoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (8n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (8o), (Z)-5- (3,4,5-Trimethoxybenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (8p), (Z)-5-(2-Bromo-5-methoxybenzylidene)- 2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8t), (Z)-5-(2- Chloro-5-nitrobenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (8u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (8v), (Z)-5- (4-Dimethylaminebenzylidene)-2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (8y), (Z)-5-(4-Dimethylamine-2-nitrobenzylidene)- 2-(3,4-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (8z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x1), (Z)-5-[5- (4-Chlorophenyl)furan-2-il-Methylen]-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (8x2), (Z)-5- [5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(3,4- dimethoxyphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x3), (Z)-5- [5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x5), (Z)-5-[5- (4-Nitrophenyl)furan-2-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x6), (Z)-5- [(1-Acetyl)-1H-indol-3-il-Methylen]-2-(3,4- 10Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x8), (Z)-5- [(2-Methyl)-1H-indol-3-il-Methylen]-2-(3,4- Dimethoxyfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (8x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-(3,4-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (8x10), 5-Benzylidene-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9a), (Z)- 5-(4-Fluorobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (9b), (Z)-5-(2-Chlorobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9c), (Z)- 5-(4-Chlorobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (9d), (Z)-5-(2,4-Dichlorobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9e), (Z)- 5-(4-Bromobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (9f), (Z)-5-(3-Nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9g), (Z)-5-(4-Nitrobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (9h), (Z)-5-(4-MethylBenzylidene)-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9i), (Z)-5- (4-Trifluoromethylbenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2- b]-1,2,4-triazole-6(5H)-one (9j), (Z)-5-(2-Methoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9k), (Z)- 5-(4-Methoxybenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one (9l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9m), (Z)- 5-(2,5-DimethoxyBenzylidene)-2-(2-trifloroMethylfenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (9n), (Z)-5-(3,4-Dimethoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9o), (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9p), 11(Z)-5-(2-Bromo-5-methoxybenzyl- den)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9r), (Z)- 5-(4-Trifluoromethoxybenzyl- den)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9s), (Z)- 5-(4-Chloro-3-trifloroMethylBenzylidene)-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9t), (Z)-5- (2-Chloro-5-nitrobenzylidene)-2-(2-trifluoromethylphenethyl)thiazolo[3,2- b]-1,2,4-triazole-6(5H)-one (9u), (Z)-5-(4-Chloro-3-nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9v), (Z)- 5-(4-Dimethylaminebenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9y), (Z)- 5-(4-Dimethylamine-2-nitrobenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (9z), (Z)- 5-[5-Phenylfuran-2-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x2), (Z)-5- [5-(2,5-(5-Dichlorophenyl)furan-2-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9x3), (Z)-5-[5-(3,4-Dichlorophenyl)furan-2-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x4), (Z)-5-[5-(2-Nitrophenyl)furan-2-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x5), (Z)-5- [5-(4-Nitrophenyl)furan-2-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x6), (Z)-5- [(1-Acetyl)-1H-indol-3-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(2- trifloroMethylfenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (9x8), (Z)-5- [(2-Methyl)-1H-indol-3-yl-methylene]-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (9x9), 12(Z)-5-(2,3-Methylenedioxybenzylidene)-2-(2- trifluoromethylphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (9x10), (Z)-5-Benzylidene-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (10a), (Z)-5-(4-FloroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (10b), (Z)-5-(2-ChloroBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10c), (Z)-5-(4- ChloroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (10d), (Z)-5-(2,4-DiChloroBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10e), (Z)-5-(4- BromoBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (10f), (Z)-5-(3-NitroBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10g), (Z)-5-(4- NitroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (10h), (Z)-5-(4-MethylBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (10i), (Z)-5-(4-Trifluoromethylbenzylidene)-2- (4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10j), (Z)-5-(2- Methoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one (10k), (Z)-5-(4-Methoxybenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10l), (Z)-5-(2,3- Dimethoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2- b][1,2,4]triazole-6(5H)-one (10m), (Z)-5-(2,5-Dimethoxybenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (10n), (Z)-5-(3,4- Dimethoxybenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b][1,2,4]triazol- 6(5H)-one (10o), (Z)-5-(3,4,5-TriMethoxyBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10p), (Z)-5-(2- Bromo-5-methoxybenzyl- den)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (10r), (Z)-5-(4-Trifluoromethoxybenzyl- den)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10s), (Z)-5-(4- Chloro-3-trifluoromethylbenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2- b]-1,2,4-triazole-6(5H)-one (10t), (Z)-5-(2-Chloro-5-nitrobenzylidene)-2- (4-cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (10u), (Z)-5- 13(4-Chloro-3-nitrobenzylidene)-2-(4-cyanophenethyl)thiazolo[3,2-b]-1,2,4- triazole-6(5H)-one (10v), (Z)-5-(4-Dimethylaminebenzylidene)-2-(4- cyanophenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10y), (Z)-5-(4- Dimethylamine-2-nitroBenzylidene)-2-(4-siyanofenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (10z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-(4- siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2- il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x3), (Z)-5-[5-(3,4-Dichlorophenyl)furan-2-yl-methylene]-2-(4- cyanophenethyl)thiazolo[3,2-b][1,2,4]triazole-6(5H)-one (10x4), (Z)-5-[5- (2-Nitrophenyl)furan-2-yl-methylene]-2-(4-cyanophenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x5), (Z)-5-[5-(4-Nitrophenyl)furan-2-il- Methylen]-2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x6), (Z)-5-[(1-Acetyl)-1H-indol-3-il-Methylen]-2-(4- siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x7), (Z)-5-[(1- Methyl)-1H-indol-3-il-Methylen]-2-(4-siyanofenethyl)thiazolo[3,2- b][1,2,4]triazol-6(5H)-one (10x8), (Z)-5-[(2-Methyl)-1H-indol-3-il- Methylen]-2-(4-siyanofenethyl)thiazolo[3,2-b][1,2,4]triazol-6(5H)-one (10x9), (Z)-5-(2,3-MethylendioxyBenzylidene)-2-(4- siyanofenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (10x10), (Z)-S-(5- Benzylidenethiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il)Methyl ethanoate (11a), (Z)-S-[5-(4-FloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- on-2-il]Methyl ethanoate (11b), (Z)-S-[5-(2- ChloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11c), (Z)-S-[5-(4-ChloroBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11d), (Z)-S-[5-(2,4- DiChloroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11e), (Z)-S-[5-(4-BromoBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-il]Methyl ethanoate (11f), (Z)-S-[5-(3- NitroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl 14ethanoate (11g), (Z)-S-[5-(4-Nitrobenzylidene)thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-on-2-yl]methyl ethanoate (11h), (Z)-S-[5-(4- Methylbenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11i), (Z)-S-[5-(4-TrifloroMethylBenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11j), (Z)-S-[5-(2- MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11k), (Z)-S-[5-(4-MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-yl]methyl ethanoate (11l), (Z)-S-[5-(2,3- Dimethoxybenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11m), (Z)-S-[5-(2,5-Dimethoxybenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11n), (Z)-S-[5-(3,4- DimethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11o), (Z)-S-[5-(3,4,5-TriMethoxyBenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11p), (Z)-S-[5-(2-Bromo-5- MethoxyBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11r), (Z)-S-[5-(4-Trifluoromethoxybenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11s), (Z)-S-[5-(4-Chloro-3- Trifluoromethylbenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2- il]Methyl ethanoate (11t), (Z)-S-[5-(2-Chloro- 5nitroBenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11u), (Z)-S-[5-(4-Chloro-3-nitrobenzylidene)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11v), (Z)-S-[5-(4- Dimethylaminebenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2- yl]methyl ethanoate (11y), (Z)-S-[5-(2-Nitro-4- Dimethylaminebenzylidene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2- yl]methyl ethanoate (11z), (Z)-S-[5-(5-Phenylfuran-2-il- Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x1), (Z)-S-[5-(5-(4-Chlorophenyl)furan-2-il-Methylen)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x2), (Z)-S-[5-(5-(2,5- DiChlorophenyl)furan-2-il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)- on-2-il]Methyl ethanoate (11x3), (Z)-S-[5-(5-(3,4-DiChlorophenyl)furan-2- 15il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x4), (Z)-S-[5-(5-(3-Nitrophenyl)furan-2-il-Methylen)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x5), (Z)-S-[5-(5-(4- Nitrophenyl)furan-2-il-Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2- il]Methyl ethanoate (11x6), (Z)-S-[5-((1-Acetyl)-1H-indol-3-il- Methylen)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-il]Methyl ethanoate (11x7), (Z)-S-[5-((1-Methyl)-1H-indol-3-il-Methylen)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-on-2-yl]methyl ethanoate (11x8), (Z)-S-[5-((2-Methyl)-1H- indol-3-yl-methylene)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11x9), (Z)-S-[5-(2,3-Methylenedioxybenzylidene)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-on-2-yl]methyl ethanoate (11x10), (Z)-5- Benzylidene-2-[3-(2,5-dimethoxyphenyl)-3-oxopropyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (12a), (Z)-5-(4-FloroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12b), (Z)-5-(2-ChloroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12c), (Z)-5-(4- ChloroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (12d), (Z)-5-(2,4-DiChloroBenzylidene)-2-[3- (2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (12e), (Z)-5-(4-BromoBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12f), (Z)-5-(3- NitroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (12g), (Z)-5-(4-NitroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12h), (Z)-5-(4-MethylBenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12i), (Z)-5-(4- Trifluoromethylbenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12j), (Z)-5-(2- MethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12k), (Z)-5-(4- MethoxyBenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- 16oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12l), (Z)-5-(2,3- Dimethoxybenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12n), (Z)-5-(3,4- Dimethoxybenzylidene)-2-[3-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (12o), (Z)-5-(3,4,5- Trimethoxybenzylidene)-2-[3-(2,5-dimethoxyphenyl)-3- oxopropyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12p), (Z)-5-(2-Bromo- 5-MethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12r), (Z)-5-(4- TrifloroMethoxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12s), (Z)-5-(4-Chloro-3- trifloroMethylBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (12u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2- [3-(2,5-Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)- one (12v), (Z)-5-(4-DimethylamineBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12y), (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-[3-(2,5- Dimethoxyphenyl)-3-oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12z), (Z)-5-[5-Phenylfuran-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- 17oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x6), (Z)-5-[(1- Acetyl)-1H-indol-3-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x7), (Z)-5-[(1- Methyl)-1H-indol-3-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x8), (Z)-5-[(2- Methyl)-1H-indol-3-il-Methylen]-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[3-(2,5-Dimethoxyphenyl)-3- oxopropil]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (12x10), (Z)-5- Benzylidene-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (13a), (Z)-5-(4-FloroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13b), (Z)-5-(2- ChloroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (13c), (Z)-5-(4-ChloroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13d), (Z)-5- (2,4-Dichlorobenzylidene)-2-(2-nitro-4,5-dimethoxyphenethyl)thiazolo[3,2- b]-1,2,4-triazole-6(5H)-one (13e), (Z)-5-(4-Bromobenzylidene)-2-(2-nitro- 4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13f), (Z)- 5-(3-NitroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (13g), (Z)-5-(4-NitroBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13h), (Z)-5-(4- MethylBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (13i), (Z)-5-(4-Trifluoromethylbenzylidene)-2-(2- nitro-4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13j), (Z)-5-(2-Methoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13k), (Z)-5- (4-MethoxyBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (13l), (Z)-5-(2,3-Dimethoxybenzylidene)-2-(2-nitro- 4,5-dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13m), 18(Z)-5-(2,5-Dimethoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13n), (Z)-5- (3,4-DimethoxyBenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13o), (Z)-5- (3,4,5-TriMethoxyBenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13p), (Z)-5- (2-Bromo-5-methoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13r), (Z)-5- (4-Trifluoromethoxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13s), (Z)-5- (4-Chloro-3-trifluoromethylbenzylidene)-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13t), (Z)-5-(2- Chloro-5-nitroBenzylidene)-2-(2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (13u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2- (2-nitro-4,5-Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13v), (Z)-5-(4-DimethylamineBenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13y), (Z)-5- (4-Dimethylamine-2-nitrobenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13z), (Z)-5- [5-Phenylfuran-2-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x1), (Z)-5- [5-(4-Chlorophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13x2), (Z)-5- [5-(2,5-Dichlorophenyl)furan-2-yl-methylene]-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x3), (Z)-5- [5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x4), (Z)-5- [5-(2-Nitrophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x5), (Z)-5- [5-(4-Nitrophenyl)furan-2-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x6), (Z)-5- 19[(1-Acetyl)-1H-indol-3-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-(2-nitro-4,5- Dimethoxyfenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x8), (Z)-5- [(2-Methyl)-1H-indol-3-il-Methylen]-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazole-6(5H)-one (13x9), (Z)-5- (2,3-Methylenedioxybenzylidene)-2-(2-nitro-4,5- dimethoxyphenethyl)thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (13x10), (Z)-5- Benzylidene-2-[2-(2-butyl-amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (14a), (Z)-5-(4-FloroBenzylidene)-2-[2-(2-butyl- amino)-2-(3-Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14b), (Z)-5-(2-ChloroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14c), (Z)-5- (4-ChloroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14d), (Z)-5- (2,4-DiChloroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14e), (Z)-5- (4-BromoBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14f), (Z)-5- (3-NitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14g), (Z)-5- (4-NitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14h), (Z)-5- (4-MethylBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14i), (Z)-5- (4-TrifloroMethylBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14j), (Z)-5- (2-MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14k), (Z)-5- (4-MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14l), (Z)-5- 20(2,3-DimethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14m), (Z)-5- (2,5-DimethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14n), (Z)-5- (3,4-Dimethoxybenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14o), (Z)-5- (3,4,5-Trimethoxybenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14p), (Z)-5- (2-Bromo-5-MethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14r), (Z)-5- (4-TrifloroMethoxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14s), (Z)-5- (4-Chloro-3-trifloroMethylBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14t), (Z)-5- (2-Chloro-5-nitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14u), (Z)-5- (4-Chloro-3-nitroBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14v), (Z)-5- (4-Dimethylaminebenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14y), (Z)-5- (4-Dimethylamine-2-nitrobenzylidene)-2-[2-(2-butyl-amino)-2-(3- methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14z), (Z)-5- [5-Phenylfuran-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x1), (Z)-5- [5-(4-Chlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x2), (Z)-5- [5-(2,5-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x3), (Z)-5- [5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x4), (Z)-5- [5-(2-Nitrophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- 21Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x5), (Z)-5- [5-(4-Nitrophenyl)furan-2-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x6), (Z)-5- [(1-Acetyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x7), (Z)-5- [(1-Methyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x8), (Z)-5- [(2-Methyl)-1H-indol-3-il-Methylen]-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x9), (Z)-5- (2,3-MethylendioxyBenzylidene)-2-[2-(2-butyl-amino)-2-(3- Methoxyphenyl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (14x10), (Z)- 5-Benzylidene-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15a), (Z)-5-(4-FloroBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15b), (Z)- 5-(2-ChloroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15c), (Z)-5-(4-ChloroBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15d), (Z)- 5-(2,4-DiChloroBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15e), (Z)-5-(4- BromoBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15f), (Z)-5-(3-NitroBenzylidene)-2-[2-(5-phenyloxazole- 2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15g), (Z)-5-(4- NitroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15h), (Z)-5-(4-MethylBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15i), (Z)- 5-(4-TrifloroMethylBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15j), (Z)-5-(2- MethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15k), (Z)-5-(4-MethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15l), (Z)- 5-(2,3-DimethoxyBenzylidene)-2-[2-(5-phenyloxazole-2- 22il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15n), (Z)-5-(3,4-DimethoxyBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15o), (Z)- 5-(3,4,5-TriMethoxyBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15r), (Z)-5-(4-Trifluoromethoxybenzylidene)-2-[2- (5-phenyloxazol-2-yl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15s), (Z)-5-(4-Chloro-3-trifluoromethylbenzylidene)-2-[2-(5-phenyloxazol-2- yl)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4- triazol-6(5H)-one (15u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15v), (Z)- 5-(4-DimethylamineBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15y), (Z)-5-(4- Dimethylamine-2-nitroBenzylidene)-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (15x1), (Z)-5-[5-(4-Chlorophenyl)furan-2-il- Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (15x2), (Z)-5-[5-(2,5-DiChlorophenyl)furan-2-il-Methylen]-2- [2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x3), (Z)-5-[5-(3,4-DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5- phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x4), (Z)-5-[5-(2-Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyloxazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x6), (Z)-5-[(1-Acetyl)- 1H-indol-3-il-Methylen]-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one (15x7), (Z)-5-[(1-Methyl)-1H-indol-3-il-Methylen]- 232-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x8), (Z)-5-[(2-Methyl)-1H-indol-3-il-Methylen]-2-[2-(5-phenyloxazole- 2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (15x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(5-phenyloxazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (15x10), (Z)-5-Benzylidene-2-[2-(5-phenyl- 1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16a), (Z)-5-(4-FloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16b), (Z)-5-(2- ChloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16c), (Z)-5-(4- ChloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16d), (Z)-5-(2,4- DiChloroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16e), (Z)-5-(4- BromoBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16f), (Z)-5-(3- NitroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (16g), (Z)-5-(4-NitroBenzylidene)-2-[2-(5- phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16h), (Z)-5-(4-MethylBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16j), (Z)-5-(2- MethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16k), (Z)-5-(4- MethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16l), (Z)-5-(2,3- DimethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16m), (Z)-5-(2,5- DimethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16n), (Z)-5-(3,4- 24DimethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16r), (Z)-5-(4- TrifloroMethoxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16s), (Z)-5-(4-Chloro-3- trifloroMethylBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2- b]-1,2,4-triazol-6(5H)-one (16u), (Z)-5-(4-Chloro-3-nitroBenzylidene)-2- [2-(5-phenyl-1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (16v), (Z)-5-(4-DimethylamineBenzylidene)-2-[2-(5-phenyl- 1,3,4-oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16y), (Z)-5-(4-Dimethylamine-2-nitroBenzylidene)-2-[2-(5-phenyl-1,3,4- oxadiazole-2-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16z), (Z)-5- [5-Phenylfuran-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x6), (Z)-5-[(1-Acetyl)- 1H-indol-3-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x7), (Z)-5-[(1-Methyl)- 251H-indol-3-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x8), (Z)-5-[(2-Methyl)- 1H-indol-3-il-Methylen]-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(5-phenyl-1,3,4-oxadiazole-2- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (16x10), (Z)-5-Benzylidene- 2-[2-(6-bromo-4-oxo-4H-chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one (17a), (Z)-5-(4-FloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H- chromene-3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17b), (Z)-5- (2-ChloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17c), (Z)-5-(4- ChloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17d), (Z)-5-(2,4- DiChloroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17e), (Z)-5-(4- BromoBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17f), (Z)-5-(3- NitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17g), (Z)-5-(4- NitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17h), (Z)-5-(4- MethylBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17i), (Z)-5-(4- TrifloroMethylBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17j), (Z)-5-(2- MethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17k), (Z)-5-(4- MethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17l), (Z)-5-(2,3- DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17m), (Z)-5-(2,5- 26DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17n), (Z)-5-(3,4- DimethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17o), (Z)-5-(3,4,5- TriMethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17p), (Z)-5-(2-Bromo-5- MethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17r), (Z)-5-(4- TrifloroMethoxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17s), (Z)-5-(4-Chloro-3- trifloroMethylBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17t), (Z)-5-(2-Chloro-5- nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17u), (Z)-5-(4-Chloro-3- nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17v), (Z)-5-(4- DimethylamineBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17y), (Z)-5-(4- Dimethylamine-2-nitroBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17z), (Z)-5-[5- Phenylfuran-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x1), (Z)-5-[5-(4- Chlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x2), (Z)-5-[5-(2,5- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene- 3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x3), (Z)-5-[5-(3,4- DiChlorophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene- 3-il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x4), (Z)-5-[5-(2- Nitrophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x5), (Z)-5-[5-(4- Nitrophenyl)furan-2-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- 27il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x6), (Z)-5-[(1-Acetyl)- 1H-indol-3-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x7), (Z)-5-[(1-Methyl)- 1H-indol-3-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x8), (Z)-5-[(2-Methyl)- 1H-indol-3-il-Methylen]-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x9), (Z)-5-(2,3- MethylendioxyBenzylidene)-2-[2-(6-bromo-4-oxo-4H-chromene-3- il)ethyl]thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one (17x10).

3. A pharmaceutical formulation / composition which comprises at least one compound according to any one of Claim 1 or 2.

4. A drug which comprises at least one compound according to any one of Claim 1 or 2.

5. A method (100) according to any one of the preceding claims; characterized in that specific 2-substituted-5-arylidenethiazolo[3,2-b]-1,2,4-triazole- 6(5H)-one derivatives -which enable EGFR inhibition, which is involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition- are synthesized by the steps of - synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); - synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); - synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); and - synthesizing 2-substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol- 6(5H)-one compounds (4a-17z) from suitable triazole compounds (4- 17) (104).

286. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); a 30 mmol of carboxylic acid compound (1 (R1-COOH)) is dissolved with a 30-40 mL of tetrahydrofuran and the mixture is prepared by adding N- hydroxysuccinimide dissolved in tetrahydrofuran in a ratio of 1:1 mol.

7. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); the reaction medium is stirred with a magnetic stirrer for 8-12 hours in an ice bath by adding dicyclohexylcarbodiimide (DCC) dissolved in tetrahydrofuran in a ratio of 1:1.25 mol.

8. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); the DCC solution is added to the reaction medium at five-minute intervals for one hour.

9. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); after the reaction is completed, it is kept at 2-4 °C overnight and then the tetrahydrofuran is evaporated at low pressure after the dicyclohexyl urea precipitated in the medium is removed by being filtered under vacuum.

10. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted succinimide compounds (2) starting from carboxylic acid compound (1) (101); the obtained oily substance is solidified by taking it in an ice bath and adding cold diethyl ether 29onto it, and the formed solid substance, i.e. succinimide compounds (2), is dried by being filtered.

11. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); the succinimide compound (2) is dissolved in tetrahydrofuran.

12. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); thiosemicarbazide dissolved in dimethyl sulfoxide (DMSO) is added onto it in a ratio of 1:1 mol and heated under a reflux cooler for 8-12 hours.

13. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); after the reaction is finished, it is kept at 2-4 °C overnight.

14. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing substituted thiosemicarbazide compounds (3) from suitable succinimide compound (2) (102); the tetrahydrofuran is evaporated at low pressure after the solid precipitated in the reaction medium is filtered and the product, i.e. thiosemicarbazide compounds (3), is precipitated by adding ice to the remaining part.

15. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); a 10% KOH is added onto the thiosemicarbazide compound (3) and heated under a reflux cooler for 3-6 hours. 3016. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); the amount of KOH solution that will be added to the reaction medium is determined in such a way that a 20-25 mL KOH solution is added onto every 10 mmol of thiosemicarbazide compound.

17. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); the solid portion that is not dissolved in the medium is removed by being filtered after the reaction is finished.

18. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 3-substituted-1,2,4-triazole-5-thione compounds (4-17) from suitable thiosemicarbazide compound (3) (103); the pH is adjusted to 4 by adding concentrated hydrochloric acid dropwise onto the filtrate in an ice bath and the precipitated product, i.e.3-substituted-1,2,4- triazole-5-thione compounds (4-17), is washed with distilled water by being filtered under vacuum and purified by crystallization with ethanol after being dried.

19. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 2-substituted-5-arylidene-thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one compounds (4a-17z) from suitable triazole compounds (4-17) (104); chloroacetic acid, anhydrous sodium acetate, concentrated acetic acid, acetic anhydride and substituted benzaldehyde are added onto the appropriate triazole compound (4-17) in a ratio of 1:1 mol and heated in an oil bath under a reflux cooler at 120-140 °C for 3-6 hours. 3120. A method (100) according to any one of the preceding claims; characterized in that in the step of synthesizing 2-substituted-5-arylidene-thiazolo[3,2-b]- 1,2,4-triazol-6(5H)-one compounds (4a-17z) from suitable triazole compounds (4-17) (104); the solid portion is removed by being filtered after the reaction is completed and the product crystallized from the medium, i.e. 2-Substituted-5-arylidene-thiazolo[3,2-b]-1,2,4-triazol-6(5H)-one compounds (4a-17z), is removed by being filtered and purified by crystallization in acetonitrile. 32ABSTRACT COMPOUNDS FOR INHIBITING EGFR AND SYNTHESIS METHOD OF THE COMPOUNDS The present invention relates to specific 2-substituted-5-arylidenethiazolo[3,2-b]- 1,2,4-triazole-6(5H)-one compounds (4a-17z) which enable EGFR (Epidermal Growth Factor Receptor) inhibition, which is known to be involved in the pathogenesis of cancer disease and is one of the mechanisms playing a role in tyrosine kinase enzyme inhibition, and to a synthesis method (100) of the compounds (4a-17z). 33

Citation Information

Patent Citations

  • Combined treatment with an EGFR kinase inhibitor and an agent that sensitizes tumor cells to the effects of EGFR kinase inhibitors

    US20100166776A1